Patent ID: 6774238
Filing Date: 2004-08-10
Classification: C07D

Abstract:
A process for the preparation of a compound of formula I by the reaction of an arylboronic acid or ester of formula III Râ€”B(OR1)(OR2)â€ƒâ€ƒ(III) where R1 and R2 are independently hydrogen, alkyl of 1 to 12 carbon atoms, or R1 and R2 together are alkylene of 2 to 4 carbon atoms;with a 5-substituted benzotriazole of formula V where X is chloro, bromo or iodo, or tosylate,in the presence of an effective amount of a palladium(II) catalyst at a temperature between 10 to 100Â° C., and where R is phenyl, naphthyl, biphenylyl, 9-phenanthryl or said phenyl, naphthyl, biphenylyl or 9-phenanthryl substituted by one to three alkyl of 1 to 18 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, R3Sâ€”, R3SOâ€”, R3SO2, aryl of 6 to 10 carbon atoms, perfluoroalkyl of 1 to 12 carbon atoms, halogen, nitro, cyano, carboxyl, alkoxycarbonyl of 2 to 19 carbon atoms, hydroxyl, alkoxy of 1 to 18 carbon atoms, aryloxy of 6 to 10 carbon atoms, aralkoxy of 7 to 15 carbon atoms, vinyl, acetyl, acetamido, amino, dialkylamino of 2 to 12 carbon atoms, formyl, thioalkoxy of 1 to 18 carbon atoms, hydroxymethyl, aminomethyl, halomethyl, sulfato, phosphato or where any two substituents form a benzo ring with the aryl moiety to which they are attached, R3 is alkyl of 1 to 18 carbon atoms, phenylalkyl of 7 to 15 carbon atoms or aryl of 6 to 10 carbon atoms, E1 is hydrogen, straight or branched alkyl of 1 to 24 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E2 is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; or E2 is alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms substituted by one or more â€”OH, â€”OCOE3, â€”NH2, â€”NHCOE3 or â€”COOE3, or mixtures thereof; or said alkyl or said alkenyl interrupted by one or more â€”Oâ€” which can be unsubstituted or substituted by one or more â€”OH groups; where E3 is hydrogen or alkyl of 1 to 24 carbon atoms, and where said alkyl is interrupted by one or more â€”Oâ€” and which can be substituted by one or more â€”OH or â€”OR21 groups where R21 is alkyl of 1 to 12 carbon atoms; and with the proviso that when E1 is hydrogen or alkyl, R is not phenyl.