Pyridine → HCID 23114764, compound

Participants

Reaction Steps

Under ice cooling, methanesulfonyl chloride (12 μl, 0.157 mmol) was added to a methylene chloride (5 ml) solution of [4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-5-fluoropyridin-2-yl]amine (54 mg, 0.131 mmol) and pyridine (16 μl, 0.197 mmol). The resulting mixture was stirred at room temperature for 7 hours, followed by the addition of pyridine (16 μl, 0.197 mmol) and methanesulfonyl chloride (12 μl, 0.157 mmol). After the reaction mixture was stirred at room temperature for 17 hours, pyridine (16 μl, 0.197 mmol) and methanesulfonyl chloride (12 μl, 0.157 mmol) were added thereto. The resulting mixture was stirred at room temperature for 2 hours and then, pyridine (16 μl, 0.197 mmol) and methanesulfonyl chloride (12 μl, 0.157 mmol) were added thereto. After the resulting mixture was stirred at room temperature for 21 hours, pyridine (16 μl, 0.197 mmol) and methanesulfonyl chloride (12 μl, 0.157 mmol) were added thereto. The resulting mixture was stirred at room temperature for 2 hour and then, concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate. The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure to give the title compound (54 mg, 0.110 mmol, 84%) as a white solid. The resulting white solid was washed with hexane-ether, and collected by filtration to afford the title compound as a white powder.

Provenance & Evidence