(Diethylamino)sulfur trifluoride → 1-[5-fluoromethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one

Participants

Reaction Steps

To a solution of 1-[5-hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (41 mg, 0.10 mmol) in DCM (1 mL) was added DAST (32 mg, 0.20 mmol) at 0° C. The final solution was stirred at ambient temperature for 12 h then washed with sat. NaHCO3 and brine. The organic layer was dried over MgSO4 and evaporated. The residue was purified by slash chromatography (hexanes:EtOAc 2:1 to 1:1) to give 32 mg (78%) of 1-[5-fluoromethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one as a white solid.

Provenance & Evidence