Dimethylformamide → 5-[[(4-Chlorophenyl)thio](2,5-difluorophenyl)methyl]-4-methyl-2-pyridinecarboxaldehyde

Participants

Reaction Steps

In an argon atmosphere, a hexane solution of n-butyllithium (1.60 M, 2.52 ml, 4.03 mmol) was added to a solution of 2-bromo-5-[[(4-chlorophenyl)thio](2,5-difluorophenyl)methyl]-4-methylpyridine (1.48 g, 3.36 mmol) in toluene (40 ml) at −78° C. The reaction mixture was stirred for 1 hour, and then N,N-dimethylformamide (0.312 ml, 4.03 mmol) was added at the same temperature. After stirring the reaction mixture for 30 minutes, water was added thereto at the same temperature, and the mixture was allowed to warm to room temperature. Ethyl acetate was added to the reaction mixture, and the resulting mixture was washed with saturated aqueous ammonium chloride, and then with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=10:1 was concentrated under reduced pressure, to obtain the title compound mg, 1.07 mmol, 32%) as a white solid.

Provenance & Evidence