Potassium Carbonate → 5-((5-(2-(3,4-Dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-2-fluorobenzonitrile

Participants

Reaction Steps

To a pre-stirred mixture of 5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2(3H)-thione (1.50 g, 3.93 mmol) and K2CO3 (0.82 g, 5.90 mmol) in acetone (60 mL) was added 5-(bromomethyl)-2-fluorobenzonitrile (1.09 g, 5.11 mmol), and the reaction mixture was heated at reflux 2 h. After cooling, the reaction mixture was filtered through Celite™ and concentrated. Purification by flash chromatography (Hex/EtOAc, 2:1) afforded the title product (1.74 g, 3.38 mmol, 86%) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 1.53 (s, 6H) 4.21 (s, 2H), 6.36 (m, 2H), 6.84 (m, 3H), 6.96 (s, 1H), 7.11 (t, 1H), 7.18 (s, 1H), 7.26 (d, 1H), 7.52 (m, 2H); MS (EI) m/z 514 (MH+).

Provenance & Evidence