METHOD OF PRODUCING PHENYL-SUBSTITUTED HETEROCYCLIC DERIVATIVE VIA COUPLING METHOD USING PALLADIUM COMPOUND Russian patent published in 2015 - IPC C07D277/20 C07D277/56 C07D275/03 C07D263/12 C07D213/79 

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing a phenyl-substituted heterocyclic derivative of formula which includes reacting a compound of formula where R¹ is a hydrogen atom or a halogen atom; R² is a hydrogen atom, cyano group, nitro group, halogen atom, formyl group or halomethyl group; A is a hydrogen atom, (C₁-C₈)-alkyl group, (C₃-C₆)-cycloalkyl group, phenyl group, fluorine atom (only when X is a bond) or a protective group for a hydroxyl group (only when X is an oxygen atom), A can be substituted with 1-3 substitutes, such substitutes including a group selected from a group consisting of a halogen atom, (C₁-C₄)-alkyl group, (C₁-C₄)-alkoxy group, (C₁-C₄)-alkylthio group, (C₃-C₆)-cycloalkyl group, phenyl group, phenoxy group and pyridyl group; X is a bond (only when A is a phenyl group or a fluorine atom) of an oxygen atom; and Y is a leaving group, and a compound of formula where H is a hydrogen atom; R³ is -COOR^3a or -COR^3b; R^3a is a hydrogen atom, (C₁-C₄)-alkyl group or a protective ester group for a carboxyl group; R^3b is an amide protective group for the carboxyl group, which forms an amide with an adjacent carbonyl group; R⁴ is a hydrogen atom, a halogen atom, (C₁-C₄)-alkyl; in the presence of (i) a palladium compound, (ii) a ligand capable of coordinating to the palladium compound or a salt thereof, (iii) a base, (iv) a (C₁-C₄₀)-carboxylic acid or salt thereof, (v) at least one additive selected from a group consisting of copper and salts thereof and complexes thereof and silver and complexes thereof.

EFFECT: obtaining a phenyl-substituted heterocyclic derivative with direct coupling of the phenyl ring of the phenyl-containing derivative and heterocyclic derivative in the position of the C-H bond of the heterocycle with high substrate selectivity.

5 cl, 10 tbl, 5 ex