Potassium Carbonate → 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide

Participants

Reaction Steps

A mixture of 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (2.0 g, 4.72 mmol), prepared in the previous step, potassium carbonate (3.26 g, 23.6 mmol) and bromoacetonitrile (0.39 mL, 5.67 mmol) in 60 mL of DMF was stirred under nitrogen at room temperature for 24 h (overnight). The reaction was partitioned between ethyl acetate and water. The organic layer was separated, extracted five times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (2.06 g, 94.5%) as a tan solid, mp 148-150° C.

Provenance & Evidence