Pyridine → 1-(3-Fluorophenyl)-N-methoxy-N,3-dimethyl-1H-indole-2-carboxamide

Participants

Reaction Steps

Activated molecular sieves (18 g) 4 Å were placed in an oven dried flask and cooled to room temperature under nitrogen. To the flask was charged with N-methoxy-N,3-dimethyl-1H-indole-2-carboxamide (1.5 g, 6.9 mmol), (3-fluorophenyl)boronic acid (2.9 g, 21 mmol), cupric acetate (1.9 g, 10 mmol), methylene chloride (130 mL) and pyridine (2.2 mL, 27 mmol). The reaction mixture was stirred at room temperature for 2 days. The mixture was filtered through a pad of Celite. The filtrate was concentrated and purified on silica gel (eluting with 0-30% EtOAc/hexane) to give the desired product (0.27 g, 12%). LCMS calculated for C18H18FN2O2(M+H)+: m/z=313.1. Found: 313.0.

Provenance & Evidence