Potassium Carbonate → N-benzyl-N-{[3'-bromo-4'-(cyanomethoxy)-1,1'-biphenyl-4-yl]methyl}-1-methyl-1H-indole-3-carboxamide

Participants

Reaction Steps

A mixture of N-benzyl-N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-1-methyl-1H-indole-3-carboxamide (1.5 g, 2.85 mmol), prepared in the previous step, bromoacetonitrile (240 μL, 3.44 mmol) and potassium carbonate (1.95 g, 14.1 mmol) in 75 mL of DMF was stirred under nitrogen at room temperature for 23 h. The reaction was partitioned between methylene chloride and water. The organic layer was separated, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give N-benzyl-N-{[3′-bromo-4′-(cyanomethoxy)-1,1′-biphenyl-4-yl]methyl}-1-methyl-1H-indole-3-carboxamide (1.2 g, 75%) as a white solid, MS (ESI) m/z 564 [M+H]+. Elemental Analysis for C32H26BrN3O2: Calc'd: C, 68.09; H, 4.64; N, 7.44; Found: C, 66.78; H, 4.68; N, 7.19.

Provenance & Evidence