Dimethylformamide → 2,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

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Reaction Steps

The 2,5-dichloro-4-[(2,5-difluorophenyl)-hydroxymethyl]pyridine (580 mg, 2.0 mmol) obtained in Referential Example 24 was dissolved in thionyl chloride (3.0 ml). To the resulting solution was added a catalytic amount of dimethylformamide. The resulting mixture was stirred for 17 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added toluene, followed by further concentration. The residue was dissolved in dimethylformamide (10 ml). To the resulting solution were added 4-chlorobenzenethiol (375 mg, 2.6 mmol) and potassium carbonate (414 mg, 3 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at 50° C. for 17 hours. After the reaction mixture was cooled to room temperature, diethyl ether (60 ml) was added thereto. The resulting mixture was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel chromatography (hexane:ether=10:1) to give the title compound (484 mg, 58%) as a solid.

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