Dimethylformamide → 7-(Benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-(benzyloxy)-5-bromo-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole (1.00 g, 2.66 mmol, Step 3), zinc cyanide (376 mg, 3.20 mmol), and tetrakis(triphenylphosphine)palladium (154 mg, 0.13 mmol) in N,N-dimethylformamide (15 mL) was stirred at 90° C. for 3 hours under nitrogen gas. After cooling to room temperature, the mixture was poured onto saturated potassium carbonate aqueous solution (100 mL), and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residual solid was washed with ethyl acetate/diisopropyl ether (1:2) to afford the title compound as a white solid (648 mg, 76%).

Provenance & Evidence