Potassium Phosphate, Tribasic → 2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-4-phenyl-1H-imidazole

Participants

Reaction Steps

A mixture of 4-bromo-2-(2-chloro-6-fluorobenzylthio)-5-(2-(3,4-dichlorophenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (100 mg, 0.166 mmol), phenylboronic acid (40.5 mg, 0.332 mmol), Pd(OAc)2 (2 mg, 0.008 mmol), tris(2-methoxyphenyl)phosphine (6 mg, 0.017 mmol), and K3PO4 (106 mg, 0.498 mmol) in EtOH—H2O (3 mL, 10:1 v/v) was refluxed overnight. The reaction mixture was filtered through Celite™. The filtrate was concentrated in vacuo, dissolved in DCM (5 mL) and washed with H2O (5 mL). The organic layer was dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (Hex/EtOAc=9:1) to give the title product (17 mg, 17%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.23 (s, 6H), 4.57 (s, 2H), 6.10 (m, 2H), 6.30 (t, 2H), 6.50 (dd, 1H), 6.75 (m, 1H), 6.80 (d, 1H), 6.85 (dd, 1H), 7.19 (m, 1H), 7.25 (t, 2H), 7.70 (s, 1H), 7.71 (s, 1H); MS (EI) m/z 601 [M+H]+.

Provenance & Evidence