METHOD FOR PRODUCING HETEROCYCLIC COMPOUNDS OF 1,3-BENZODIOXOL Russian patent published in 2021 - IPC C07D495/10 

FIELD: medicine.

SUBSTANCE: invention relates to a method for producing a compound of the formula (I), in which R₁ is selected from CHF₂ and CF₃, and Q is selected from chlorine, bromine and fluorine, including each of following stages: (1) conducting a reaction of a compound of the formula (II), in which R₂ is selected from C_1-6-alkyl and arylalkyl, R₂₁ is C(O)CH₃; with a compound of the formula (III), in which is a single bond, a double bond or two single bonds, and, in cases when is a double bond or two single bonds, is a single bond, and, in cases when is a single bond, is a double bond; R₃ is oxygen in cases when is a double bond, and R₃ is O-C_1-6-alkyl in cases when is a single bond or two single bonds; in the presence of an acid catalyst to form a compound of the formula (IV); (2a) conducting a reaction of the resulting compound of the formula (IV) with aromatic or aliphatic thiol in a solvent in the presence of a base to form a compound of the formula (VI); (2b) conducting a reaction of the compound of formula (VI) with aqueous N(Bu)₄⁺OH^- to form a compound of the formula (VII); (3) alkylating the resulting compound of the formula (VII) with a hydrochlorofluorocarbon reagent R₁-Cl (VIII) in the presence of a polar solvent, where R₁ corresponds to the above-mentioned definitions, before the formation of a compound of the formula (IX); (4) conducting a reaction of the compound of the formula (IX) with a pyridine compound of the formula (X), in which Q_X is selected from chlorine, bromine, fluorine and iodine, in the presence of a polar solvent in the presence of a base to form a compound of the formula (XI); and (5) oxidizing the resulting compound of the formula (XI) to form a compound of the formula (I). The invention also relates to intermediate compounds of the formula (VI), formula (VII), formula (IX).

EFFECT: new method is developed for producing a compound of the formula (I) with increased purity and yield, which can be used in medicine for use as PDE4 inhibitors.

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