Triphenylphosphine → 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

Participants

Reaction Steps

To a solution of 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (400 mg, 1.06 mmol) in anhyd THF (1.2 mL) were added PPh3 (347 mg, 1.32 mmol), (4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorophenyl)methanol (458 mg, 1.37 mmol) and DIAD (275 μL, 1.32 mmol). The reaction was stirred for 24 h and monitored by LCMS. The reaction mixture was partitioned in EtOAc and H2O. The organic layer was washed with brine, concentrated under reduced pressure, and purified by flash chromatography (45% EtOAc/Hex) to give 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (620 mg, 87%). MS (EI) m/z 677.40 (MH+).

Provenance & Evidence