Triethylamine → 3-(4-Fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid 3-trifluoromethyl-benzylamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-bromo-3-(4-fluorophenyl)-imidazo[1,5-a]pyridine (0.100 g, 0.344 mmol), Et3N (95.0 μL, 0.683 mmol), 3-(trifluoromethyl)benzylamine (89.0 μL, 0.621 mmol), Pd[PhCN]2Cl2 (5.0 mg, 0.013 mmol), and dppf (21 mg, 0.038 mmol) in degassed toluene (10 mL) is placed in a pressure reactor. The stirred mixture is placed under 15 bars of carbon monoxide and warmed at 140° C. After 3 hours, the pressure reactor is cooled to room temperature, returned to atmospheric pressure and opened. The reaction mixture is diluted with saturated aqueous ammonium chloride (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layers are washed with saturated aqueous ammonium chloride (3×10 mL), brine (10 mL), dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0-50% EtOAc in dichloromethane. The resulting solid is triturated with ether-hexanes to afford the title compound.

Provenance & Evidence