Chlorosuccinimide → 2-(4-chloro-5-phenyl-1H-imidazol-1-yl)-5-(methylsulfonyl)pyridine

Participants

Reaction Steps

5-(methylsulfonyl)-2-(5-phenyl-1H-imidazol-1-yl)pyridine (50 g), N-chlorosuccinimide (20 g) and azo-bis-isobutyronitrile (500 mg) were dissolved in 3 L tetrachloromethane to allow reflux overnight. The reaction mixture was cooled to room temperature, and the residual solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain the target compound (15 g). 1H-NMR (300 MHz, CDCl3): δ 3.12 (3H, s), 6.78 (1H, dd), 7.28 (2H, m), 7.44 (3H, m), 8.06 (1H, dd), 8.25 (1H, s), 9.03 (1H, dd); LC-MS m/z: 335 [M++1], purity (HPLC)>95%.

Provenance & Evidence