Benzoyl chloride → [1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-phenylmethanone

Participants

Reaction Steps

Benzoyl chloride (180 μl, 1.52 mmol) was slowly added to a stirred slurry of aluminum chloride (223 mg, 1.67 mmol) in methylene chloride (15 ml) at -10° C. After 30 minutes, a solution of 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (Example 1) (500 mg, 1.52 mmol) in methylene chloride (10 ml) was added. The reaction mixture was warmed to room temperature and stirred for 20 hours. The reaction mixture was poured over ice-water and extracted with methylene chloride. The organic fraction was washed with brine, dried (MgSO4), filtered and concentrated. The crude yellowish solid (570 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give [1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrol-3-yl]-phenylmethanone (54 mg, 8%) as a white solid: Anal Calc'd. for C25H20NSFO3 ·0.5 H2O: C, 67.86; H, 4.78; N, 3.17. Found: C, 67.59; H, 4.70; N. 3.07.

Provenance & Evidence