Boron tribromide → 3-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-ol

Participants

Reaction Steps

To a stirred solution of 1-cyclohexylmethyl-5,6-difluoro-2-[2-(4-methoxy-benzyloxy)-pyridin-3-yl]-1H-benzoimidazole (2.32 g, 5 mmol) in dichloromethane (40 ml) was added boron tri bromide (1M solution in dichloromethane; 21 ml, 21 mmol) at 25° C., and the resulting mixture was allowed to stir for 16 h at the same temperature. The reaction mixture was then quenched with saturated aqueous solution of sodium bi carbonate solution, further diluted with dichloromethane (30 ml). Organic layer was washed with water, and then with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure to afford the crude material. Crude product was purified by column chromatography using silica gel (5-10% ethyl acetate/n-hexane) to give the title compound as a colorless solid (39%). MS (Turbo Spray): m/z=344.3 (M+H).

Provenance & Evidence