The invention relates to a method for producing compounds according to formula (I), wherein the hydrogen atom bound to the nitrogen is replaced with a metal atom from the series of alkali metals or alkaline-earth metals or with an aluminum atom or a tetraalkylammonium cation and wherein the alkaline-earth metal salts or the aluminum salts of the compound (I) can contain other anions such as fluoride, chloride, bromide, iodide, or sulfate in addition to a deprotonated anion (I).
C07D 265/18 - Oxazines-1, 3Oxazines-1, 3 hydrogénées condensées avec des carbocycles ou avec des systèmes carbocycliques condensées avec un cycle à six chaînons avec des hétéro-atomes liés directement en position 2
2.
METHOD FOR THE ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC CARBON NUCLEOPHILES TO TRIFLUOROMETHYL KETONES AND USE OF THE METHOD IN THE SYNTHESIS OF HIV REVERSE TRANSCRIPTASE INHIBITORS
The invention relates to a method for producing compounds of the formula A1, wherein the carbon atom to which both the CF3 group and the hydroxy group are bonded is a stereocenter having either the R or the S configuration and wherein R1 and R2 are a C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, C4-C8 cycloalkenyl, C2-C8 alkynyl, C6-C14 aryl, or C5-C13 heteroaryl group independently of each other, wherein the alkyl, alkenyl, and alkynyl groups are straight-chained or branched and wherein all stated groups are unsubstituted or are mono- or polysubstituted with the same or different substituents selected from the group: halide, NO2, SO3H, SO3Na, SO3K, CN, OH, NH2, NH-lower alkyl, N-di-lower alkyl, COOH, COO-lower alkyl, lower alkyl, and C3-C6 cycloalkyl, and wherein terminal OH-, NH2-, and NH-lower alkyl groups and acidic H atoms are unprotected or are protected with a protective group, wherein a mixture of a zinc(II) salt, an enantiomerically pure or enantiomerically enriched auxiliary of the formula (I), wherein R3 and R4 are C6-C14 aryl, C5-C13 heteroaryl, C1-C8 alkyl, or C2-C8 alkenyl groups or hydrogen independently of each other and R5 and R6 are C6-C14 aryl, C5-C13 heteroaryl, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl groups or hydrogen independently of each other or R5 and R6 together represent a C3-C7 alkylene or C3-C7 alkenylene group and at least one of the centers C1, C2, preferably both, is a stereocenter regardless of the configuration of the other center and has either the R or the S configuration and a second auxiliary, which is selected from the group comprising the alcohols, phenols, mercaptans, amines, carboxylic acids, urea derivatives, or the heterocycles containing nitrogen, oxygen, or sulfur, is reacted with an organic or inorganic base and then is reacted with an organometallic compound R1 -M in which R1 has the meaning specified above and in which M is selected from the group: lithium, sodium, potassium, magnesium halide, magnesium cyanide, magnesium-lower alkyl-alcoholates, and then is reacted with a trifluoromethyl ketone (II), wherein R2 has the meaning stated above.
C07D 265/18 - Oxazines-1, 3Oxazines-1, 3 hydrogénées condensées avec des carbocycles ou avec des systèmes carbocycliques condensées avec un cycle à six chaînons avec des hétéro-atomes liés directement en position 2
C07C 215/70 - Composés contenant des groupes amino et hydroxy liés au même squelette carboné ayant des groupes amino liés à des atomes de carbone de cycles aromatiques à six chaînons et des groupes hydroxy liés à des atomes de carbone acycliques ou a des atomes de carbone de cycles, autres que des cycles aromatiques à six chaînons, du même squelette carboné avec des cycles, autres que des cycles aromatiques à six chaînons, faisant partie du squelette carboné
The invention relates to a process for preparing optionally organically substituted phosphonic anhydrides directly from the corresponding phosphonic diesters, without the free phosphonic acid being required as an intermediate, according to reaction scheme (I), (II), (III), (IV), (V), (VI) wherein the substituents n, R, R1, R2 and X are each defined as specified in the description.
The present invention relates to a process for the preparation of controlled-release solid oral pharmaceutical formulations of oxcarbazepine, and the pharmaceutical formulations obtainable by said process.
A61K 31/55 - Composés hétérocycliques ayant l'azote comme hétéro-atome d'un cycle, p. ex. guanéthidine ou rifamycines ayant des cycles à sept chaînons, p. ex. azélastine, pentylènetétrazole
5.
METHOD FOR PRODUCING CYCLOPENT-4-ENE-1,3-DIOL OR CYCLOPENT-4-ENE-1,3-DIOL DERIVATIVES
The invention relates to a method for producing cis-cyclopent-4-ene-1,3-diol and cis-cyclopent-4-ene-1,3-dialkanoates by selective cis-1,2-reduction of 4-hydroxycyclopent-2-enone (I) by means of a hydroboron (II), in the presence of substoichiometric quantities of a trivalent rare earth metal compound (III), to form cyclopent-4-ene-1,3-diol (IV) which can then be optionally reacted with an acylation agent (V) to form cis-cyclopent-4-ene-1,3-dialkanoates (VI), in order to simplify the reprocessing and without intermediate isolation.
C07C 29/159 - Préparation de composés comportant des groupes hydroxyle ou O-métal liés à un atome de carbone ne faisant pas partie d'un cycle aromatique à six chaînons par réduction exclusivement des oxydes de carbone avec des agents réducteurs autres que l'hydrogène ou des gaz contenant de l'hydrogène
C07C 35/06 - Composés comportant au moins un groupe hydroxyle ou O-métal lié à un atome de carbone d'un cycle autre qu'un cycle aromatique à six chaînons monocycliques contenant des cycles à cinq chaînons
6.
METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF CHIRAL EPOXIDES BY ADH REDUCTION OF KETONES SUBSTITUTED WITH ALPHA STARTING GROUPS AND CYCLISATION
The invention relates to a method for producing chiral epoxides by reducing ketones substituted with α-starting groups with cell-free (R)- or (S)-selective alcohol dehydrogenases in the presence of a cofactor, and optionally a suitable system for the regeneration of the oxidised cofactor to form the chiral alcohols, and subsequent base-induced cyclisation to form the chiral epoxides (EQUATION 1) wherein LG can represent F, Cl, Br, I, OSO2Ar, OSO2R4 or OP(O)OR4R5 and R1, R2 and R3 independently represent hydrogen, a branched or unbranched, optionally substituted C1-C20 alkyl radical, an optionally substituted C3-C10 cycloalkyl or alkenyl radical or an optionally substituted carbocyclic or heterocyclic aryl radical or a radical from the group consisting of CO2R4, CONR4R5, COSR4, CS2R4, C(NH)NR4R5, CN, CHaI3, OAr, SAr, OR4, SR4, CHO, OH, NR4R5, Cl, F, Br, I or SiR4R5R6, where R4, R5 and R6 independently represent hydrogen, a branched or unbranched, optionally substituted C1-C20 alkyl radical, an optionally substituted C3-C10 cycloalkyl or alkenyl radical or a substituted carbocylic or heterocyclic aryl radical, the intermediately formed chiral alcohol Il not being isolated.
C07D 303/08 - Composés contenant des cycles oxirane avec des radicaux hydrocarbonés substitués par des atomes d'halogènes, des radicaux nitro ou des radicaux nitroso
7.
PROCESS FOR THE SYNTHESIS OF ARYLOXYPROPYLAMINE AND HETEROARYLOXYPROPYLAMINE
The present invention relates to a process for the synthesis of aryloxypropylamine and heteroaryloxypropylamine of formula (I) where: A is aryl or heteroaryl, where the aryl is preferably a phenyl, optionally substituted, selected from benzyl and tolyl and the heteroaryl is preferably thiophenyl; Y is an aryl, preferably phenyl, a substituted phenyl or a naphthyl, where the substituted phenyl is preferably selected from tolyl, trihalomethyltolyl and alkoxytolyl, starting from a suitable amino alcohol of formula (II).
C07C 209/68 - Préparation de composés contenant des groupes amino liés à un squelette carboné à partir d'amines, par des réactions n'impliquant pas de groupes amino, p. ex. réduction d'amines non saturées, aromatisation ou substitution du squelette carboné
C07C 217/48 - Composés contenant des groupes amino et hydroxy éthérifiés liés au même squelette carboné ayant des groupes hydroxy éthérifiés et des groupes amino liés à des atomes de carbone acycliques du même squelette carboné le squelette carboné étant non saturé et contenant des cycles
C07C 211/29 - Composés contenant des groupes amino liés à un squelette carboné ayant des groupes amino liés à des atomes de carbone acycliques d'un squelette carboné non saturé contenant au moins un cycle aromatique à six chaînons le squelette carboné étant substitué de plus par des atomes d'halogène ou par des groupes nitro ou nitroso
A process for preparing fexofenadine is described, which provides for the hydrolysis of 4-[4-[4-(hydroxydiphenylmethyl)-l-piperidyl]-l-oxobutyl]-α,α- dimethylbenzeneacetic acid-alkyl ester, in a mixture of water and optionally an organic solvent, in the presence of a base; the carboxylate salt of 4- [4- [4- (hydroxydiphenylmethyl)- 1 -piperidyl] - 1 -oxobutyl] -α,α -dimethylbenzeneacetic acid is thus obtained, which is directly reduced as carboxylate in a basic environment with hydrogen in the presence of a suitable hydrogenation catalyst to give the carboxylate of fexofenadine, which is precipitated by neutralisation of the solution.
C07D 211/22 - Composés hétérocycliques contenant des cycles pyridiques hydrogénés, non condensés avec d'autres cycles avec uniquement des atomes d'hydrogène et de carbone liés directement à l'atome d'azote du cycle ne comportant pas de liaison double entre chaînons cycliques ou entre chaînons cycliques et chaînons non cycliques avec des radicaux hydrocarbonés ou des radicaux hydrocarbonés substitués, liés directement aux atomes de carbone du cycle avec des radicaux hydrocarbonés substitués liés aux atomes de carbone du cycle avec des radicaux hydrocarbonés, substitués par des atomes d'oxygène ou de soufre liés par des liaisons simples par des atomes d'oxygène
A process for preparing fexofenadine is described, comprising the purification of 4-[4-chloro-l-oxobutyl]-2,2-dimethylphenyl acetic acid alkyl ester by means of suspension in a hydrocarbon, preferably n-heptane. The compound thus obtained is dissolved in a suitable solvent and condensed with azacyclanol to give the compound shown below (I) where R is an alkyl radical, which is then hydrolysed and reduced to give fexofenadine.
C07D 211/22 - Composés hétérocycliques contenant des cycles pyridiques hydrogénés, non condensés avec d'autres cycles avec uniquement des atomes d'hydrogène et de carbone liés directement à l'atome d'azote du cycle ne comportant pas de liaison double entre chaînons cycliques ou entre chaînons cycliques et chaînons non cycliques avec des radicaux hydrocarbonés ou des radicaux hydrocarbonés substitués, liés directement aux atomes de carbone du cycle avec des radicaux hydrocarbonés substitués liés aux atomes de carbone du cycle avec des radicaux hydrocarbonés, substitués par des atomes d'oxygène ou de soufre liés par des liaisons simples par des atomes d'oxygène
C07C 69/76 - Esters d'acides carboxyliques dont un groupe carboxyle estérifié est lié à un atome de carbone d'un cycle aromatique à six chaînons
10.
METHOD FOR THE PRODUCTION OF BORONIC ACIDS CARRYING CYANOALKYL, CARBOXYL AND AMINOCARBONYL GROUPS AND THEIR DERIVATIVES
A process for the manufacture of aminocarbonyl boronic acids of formula (IV) by converting the compounds of formula (III) with a Bronsted base Y(OH)n in a solvent or a solvent mixture, wherein Z represents an optionally substituted arylene, heteroarylene, alkene, heteroalkene, alkylidene, heteroalkylidene, alkenylidene, heteroalkenylidene, alkynylidene, arylalkylene, heteroarylalkylene, arylheteroalkylene, heteroarylheteroalkylene, alkylheteroarylene, heteroalkylheteroarylene, or alkylarylene group; Y represents a metal or ammonium cation of valence n with 0 < n < 5; and B represents boronic acid, boronic acid ester, or a borate, or a boronic acid anhydride. The aminocarbonyl boronic acids of formula (IV) can be further hydrolyzed to form the carboxy boronic acid of formula (V).
A novel method for the preparation of stavudine polymorphic form I and form II is described; it's prepared starting from 5'-acetate-2',3'-diacetyl-5-methyluridine. The 5' -acetate-2',3'-diacetyl-5-methyluridine, by reaction with catalytic amounts of sodium methoxide in a C1-C4 alcholic solvent, gives crude stavudine form II. Crude stavudine form II, which doesn't need to be isolated or purified, can be converted into polymorphic form I by slurry at reflux in isopropanol.
C07D 405/04 - Composés hétérocycliques contenant à la fois un ou plusieurs hétérocycles comportant des atomes d'oxygène comme uniques hétéro-atomes du cycle et un ou plusieurs hétérocycles comportant des atomes d'azote comme uniques hétéro-atomes du cycle contenant deux hétérocycles liés par une liaison directe de chaînon cyclique à chaînon cyclique
12.
SULFONATED PHOSPHINE LIGANDS AND PROCESS FOR CROSS-COUPLING ARYL HALIDES AND ARYLSULFONATES AND HETEROARYL HALIDES AND HETEROARYLSULFONATES WITH AMINES, ALCOHOLS AND CARBON NUCLEOPHILES BY USING THE LIGANDS IN CONJUNCTION WITH TRANSITION METAL CATALYSTS
The invention relates to sulfonated phosphine ligands of the structure and to catalyst systems comprising these ligands and to their use in cross-coupling reactions, where R1-6, X1-10, Y1, Y2, P and Q1-4 are each defined as specified.
C07F 9/655 - Composés hétérocycliques, p. ex. contenant du phosphore comme hétéro-atome du cycle comportant des atomes d'oxygène, avec ou sans atomes de soufre, de sélénium ou de tellure, comme uniques hétéro-atomes du cycle
Process for preparing compounds of the formula (III) by cross-coupling of enolizable carbonyl compounds, nitriles or their analogues of the formula (II) with substituted aryl or heteroaryl compounds of the formula (I) in the presence of a Br쇦nsted base and of a catalyst or precatalyst containing a.) a transition metal, a complex, a salt or a compound of this transition metal from the group V, Mn, Fe, Co, Ni, Rh, Pd, Ir, Pt}, and b.) at least one sulphonated phosphane ligand in a solvent or solvent mixture in accordance with scheme (1), Hal standing for fluorine, chlorine, bromine, iodine, alkoxy or a sulphonate group; X1-5 denote independently of one another carbon or nitrogen, or pairs of adjacent X and R, joined via a formal double bond, stand in unison for O, S, NH or NR’; Z stands for O, S, NR’’, NOR’’, NNR’’’R’’, or Z together with Y forms a CN group. Y can stand for a radical from the group hydrogen, methyl, linear, branched C1-C20 alkyl or cyclic, optionally substituted alkyl, substituted or unsubstituted aryl or heteroaryl, optionally substituted alkoxy, aryloxy, heteroaryloxy, optionally substituted alkylthio, arylthio, heteroarylthio, optionally substituted dialkylamino, di(hetero)arylamino, alkyl(hetero)arylamino} and with R’, R’, R’’ or R’’ may form a ring.
C07C 253/30 - Préparation de nitriles d'acides carboxyliques par des réactions n'impliquant pas la formation de groupes cyano
C07C 45/68 - Préparation de composés comportant des groupes C=O liés uniquement à des atomes de carbone ou d'hydrogènePréparation des chélates de ces composés par des réactions ne créant pas de groupe C=O par isomérisationPréparation de composés comportant des groupes C=O liés uniquement à des atomes de carbone ou d'hydrogènePréparation des chélates de ces composés par des réactions ne créant pas de groupe C=O par modification de la taille du squelette carboné par augmentation du nombre d'atomes de carbone
C07C 67/343 - Préparation d'esters d'acides carboxyliques par modification de la partie acide de l'ester sans introduction d'un groupe ester par isomérisationPréparation d'esters d'acides carboxyliques par modification de la partie acide de l'ester sans introduction d'un groupe ester par modification de la taille du squelette carboné par augmentation du nombre d'atomes de carbone
C07C 249/02 - Préparation de composés contenant des atomes d'azote, liés par des liaisons doubles à un squelette carboné de composés contenant des groupes imino
14.
PROCESS FOR PREPARING NITRILES BY ELIMINATION REACTIONS
Process for preparing nitriles of the formula (II): R-C≡N by reacting N-alkylcarboxamides (RCO-NHR1) or ammonium salts of carboxylic acids (RCOO-NH3R1+) or carboxylic acids in the presence of alkylamines or ammonium salts (RCOOH +NH2R1, RCOOH + NH3R1+), respectively, R being an arbitrarily substituted linear or branched C1-C12- alkyl radical, a C3-C12 cycloalkyl radical or an alkenyl, alkynyl or aryl or heteroaryl radical and R1 being an arbitrary substituted, linear or branched C2-C1 alkyl radical, a C3-C12 cycloalkyl radical or an alkenyl or alkynyl radical, with phosphonic anhydrides in the presence if desired of a base in an organic solvent at a temperature in the range from -30 to 180°C. The phosphonic anhydride used is in particular a 2,4,6-substituted 1,3,5,2,4,6-trioxathiaphosphinane 2,4,6-thoxide of the formula (I).
A method for producing unprotected or carbamate-protected amines of formulae (II) and (III) or R1 - NH2 (II) or R1 - NHCO2R2 (III) by reacting hydroxamic acids of formula (I) (R1 CONHOH) with a) alkylphosphonic acid anhydrite's, b) alcohol R2OH and c) optionally with a base, at a temperature ranging from 100 to +120 °C, wherein the hydroxamic acid (I) is produced prior to or during reacting (in situ) and R1 is an optionally substituted linear or branched C1C12 alkyl radical, substituted C3-C10 cycloalkyl, alkenyl, aryl or heteroaryl radical and R2 is an open-chain, cyclic or branched aIIyI, aryl or C1 to C12-alkyl radicals, or aryloxy, allyloxy or alkoxy radical possibly substituted with open-chain, cyclic or branched C1 to C12-alkyl radicals.
C07C 209/56 - Préparation de composés contenant des groupes amino liés à un squelette carboné par des réactions de réarrangement à partir d'acides carboxyliques, en impliquant un réarrangement du type Hofmann, Curtius, Schmidt ou Lossen
C07C 269/00 - Préparation de dérivés d'acide carbamique, c.-à-d. de composés contenant l'un des groupes l'atome d'azote ne faisant pas partie de groupes nitro ou nitroso
The invention relates to a method for producing substituted halopyridines (II) by reacting a ß-hydroxy-y-acyl butyronitrile (I) or a suitable acyl-protected derivative with hydrogen halides, or substances or mixtures that can release hydrogen halides. In the formulae (I) and (II): R, R4 represent H, a linear or branched alkyl group, optionally a substituted aryl group, an aralkyl group, or optionally a substituted heteroaryl group; R1, R2, R3 represent H, a linear or branched alkyl group, optionally a substituted aryl, aralkyl, optionally a substituted heteroaryl group or one of the following groups CnH(2n+1-m)Xm, COOR, or CN; R5 represents H, a linear or branched alkyl group, optionally a substituted aryl group, an aralkyl, optionally a substituted heteroaryl or one of the following groups CnH(2n+1-m)Xm, COOR, CN, SO2R, SOR, PO(OR)2; n represents a positive whole number; m represents a positive whole number that is less than or equal to 2n+1; and X represents F, Cl, Br, or I.
The invention relates to a method for producing aryl or heteroaryl amines, ethers or thioethers (III) by cross-coupling primary or secondary amines, alcohols or thioalcohols (II) with substituted aryl or heteroaryl compounds (I) in the presence of a Brζnsted base and a catalyst or a pre-catalyst containing a) a transition metal, a complex, a salt, or a compound of said transition metal from the group {V, Mn, Fe, Co, Ni, Rh, Pd, Ir, Pt}, and b) at least one sulfonated phosphane ligand in a solvent or a solvent mixture corresponding to scheme 1 wherein Hal represents fluorine, chlorine, bromine, iodine, alkoxy, trifluoromethane sulfonate, nonafluorotrimethyl-methane sulfonate, methane sulfonate, 4-toluene sulfonate, benzene sulfonate, 2-naphthaline sulfonate, 3-nitrobenzene sulfonate, 4-nitrobenzene sulfonate, 4-chlorobenzene sulfonate, 2,4,6-triisopropylbenzene sulfonate or any other sulfonate, and X represents O, S or NR'. The invention also relates to novel phosphane ligands.
C07C 41/16 - Préparation d'éthers par réactions d'esters d'acides minéraux ou organiques avec des groupes hydroxyle ou O-métal
C07C 43/275 - Éthers l'atome d'oxygène de la fonction éther étant lié à deux atomes de carbone appartenant à des cycles aromatiques à six chaînons toutes les liaisons sur l'oxygène de la fonction éther étant sur des cycles aromatiques à six chaînons
C07C 209/10 - Préparation de composés contenant des groupes amino liés à un squelette carboné par substitution de groupes fonctionnels par des groupes amino par substitution d'atomes d'halogène avec formation de groupes amino liés à des atomes de carbone de cycles aromatiques à six chaînons ou à partir d'amines ayant des atomes d'azote liés à des atomes de carbone de cycles aromatiques à six chaînons
C07C 211/56 - Composés contenant des groupes amino liés à un squelette carboné ayant des groupes amino liés à des atomes de carbone de cycles aromatiques à six chaînons du squelette carboné ayant des groupes amino liés à deux ou trois cycles aromatiques à six chaînons le squelette carboné étant substitué de plus par des atomes d'halogène ou par des groupes nitro ou nitroso
C07C 255/58 - Nitriles d'acides carboxyliques ayant des groupes cyano liés à des atomes de carbone de cycles aromatiques à six chaînons d'un squelette carboné contenant des groupes cyano et des atomes d'azote, liés par des liaisons simples et n'étant pas liés de plus à d'autres hétéro-atomes, liés au squelette carboné
C07D 295/02 - Composés hétérocycliques contenant des cycles polyméthylène imine d'au moins cinq chaînons, des cycles aza-3 bicyclo [3.2.2] nonane, piperazine, morpholine ou thiomorpholine, ne comportant que des atomes d'hydrogène liés directement aux atomes de carbone du cycle contenant uniquement des atomes d'hydrogène et de carbone en plus des hétéro-éléments du cycle
C07C 281/02 - Composés contenant l'un des groupes p. ex. carbazates
C07C 253/30 - Préparation de nitriles d'acides carboxyliques par des réactions n'impliquant pas la formation de groupes cyano
18.
METHOD FOR PRODUCING SINGLE ENANTIOMER EPOXIDES BY THE ADH REDUCTION OF ALPHA-LEAVING GROUP-SUBSTITUTED KETONES AND CYCLISATION
The invention relates to a method for producing single enantiomer epoxides by reducing a-leaving group-substituted ketones with (R)- or (S)-selective alcohol dehydrogenases in the presence of a cofactor and optionally a suitable system for regenerating the oxidised cofactor, to produce the corresponding single enantiomer alcohols and subsequently, by means of cyclisation induced by a base, the corresponding single enantiomer epoxides (EQUATION 1 ), wherein in EQUATION 1 LG may stand for F, CI, Br, I, OSO2Ar, OSO2CH3, OSO2R or OP(O)OR2, and R1, R2 and R3, independently of one another, stand for hydrogen, a branched or unbranched, optionally substituted C1-C2O- alkyl radical, symbolise an optionally randomly substituted C3-C10- cycloalkyl or alkenyl radical or a randomly substituted carbo- or heterocyclic aryl radical, or corresponds to a radical from the group CO2R, CONR2, COSR, CS2R, C(NH)NR2, CN, CHaI3, ArO, ArS, RO, RS, CHO, OH, NHR, NR2, Cl, F, Br, I or SiR3.
C07D 303/08 - Composés contenant des cycles oxirane avec des radicaux hydrocarbonés substitués par des atomes d'halogènes, des radicaux nitro ou des radicaux nitroso
The invention relates to a method for producing furfural-4-boronic acid by the reaction of furfural acetals (I), which are substituted by halogen in position 4, with boronic acid esters or anhydrides (II), by the subsequent metalation of compound (I) and the simultaneous or subsequent reaction with a boronic acid ester or anhydride (II) to form an acetal-protected furfural-4-boronic acid ester. The product is then subjected to an acid hydrolysis, in which the acetal protection group is eliminated, to form furfural-4-boronic acid (III). In said formulae: X represents chlorine, bromine or iodine; R represents a branched, unbranched and/or cyclic, optionally substituted C1-C20 and in particular C1-C8 alkyl group, an optionally substituted C6-C12 aryl group or an optionally substituted C3-C8 cycloalkyl group, whereby the two groups R together can form a ring; R', R'', R''' independently of one another represent acylic or cyclic, branched or unbranched, optionally substituted C1-C20 alkyl groups, or optionally substituted aryl groups, whereby optionally two of the groups R', R'' and R''' together form a ring, or represent additional groups B(OR)3.
METHOD FOR PRODUCING ALKYL-SUBSTITUTED AROMATIC AND HETEROAROMATIC COMPOUNDS BY CROSS-COUPLING ALKYL BORONIC ACIDS WITH ARYL- OR HETEROARYL-HALOGENIDES OR SULFONATES UNDER PD CATALYSIS IN THE PRESENCE OF A LIGAND
The invention relates to a method for producing alkyl-substituted aromatic and heteroaromatic compounds (III) by cross-coupling alkyl boronic acids (II) with aryl- or heteroaryl-halogenides or with aryl- or heteroaryl-sulfonates (I) in the presence of a catalyst and of a Br즸nsted base in a solvent or solvent mixture, in which: Hal represents chlorine, bromine, iodine, trifluoromethanesulfonate, nonafluorotrimethyl methane sulfonate, methane sulfonate, 4-toluolsulfonate, benzene sulfonate, 2- naphthalene sulfonate, 3-nitrobenzene sulfonate, 4-nitrobenzene sulfonate, 4-chlorobenzene sulfonate or 2,4,6-triisopropylbenzene sulfonate; X1-5, independent of one another, represent carbon, XiRi represents nitrogen, or each two adjacent XiRi's bound via a formal double bond represent, together, O (furane), S (thiophene), NH or NRi (pyrrole); radicals R1-5 represent substituents from the group consisting of hydrogen, methyl, primary, secondary or tertiary, cyclic or acyclic alkyl radicals having 2 to 20 C atoms, in which optionally one or more hydrogen atoms are substituted by fluoride or chlorine or bromine, e.g. CF3, substituted cyclic or acyclic alkyl groups, hydroxy, alkoxy, amino, alkylamino, dialkylamino, arylamino, diarylamino, alkylarylamino, phenyl, substituted phenyl, heteroaryl, substituted heteroaryl, thio, alkylthio, arylthio, diarylphosphino, dialkylphosphino, alkylarylphosphino, optionally substituted aminocarbonyl, CO2-, alkyl- or aryloxycarbonyl, hydroxyalkyl, alkoxyalkyl, fluorine or chlorine, nitro, cyano, aryl- or alkylsulfone, aryl- or alkylsulfonyl} or each two adjacent radicals R1-5 represent, together, an aromatic, heteroaromatic or aliphatic fused ring; alkyl represents any linear, branched or cyclic alkyl radical having 1 to 40 C atoms, in which optionally one or more hydrogen atoms are substituted by foreign atoms or functions of the group fluorine, optionally chlorine or bromine, hydroxy, alkoxy, amino, alkylamino, dialkylamino, arylamino, diarylamino, alkylarylamino, phenyl, substituted phenyl, heteroaryl, substituted heteroaryl, thio, alkylthio, arylthio, diarylphosphino, dialkylphosphino, alkylarylphosphino, optionally substituted aminocarbonyl, CO2-, alkyl- or aryloxycarbonyl, hydroxyalkyl, alkoxyalkyl, flourine or chlorine, nitro, cyano, aryl- or alkylsulfone}, R' and R'', independent of one another, represent the same or different radicals from the group consisting of hydrogen, methyl, linear, branched or cyclic alkyl, optionally substituted, and phenyl, optionally substituted} or, together, form a ring and represent a bridging structure element from the group consisting of optionally substituted alkylene, branched alkylene, cyclic alkylene or optionally substituted azaalkylene}.
01 - Produits chimiques destinés à l'industrie, aux sciences ainsi qu'à l'agriculture
Produits et services
(1) Chemicals used in industry and science, namely an auxiliary reagent for the pharmaceutical industry and a reacting compound for flame retarding resins.
