Triethylamine → 3-(4-Fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid (2-bromopyridin-4-ylmethyl)-amide

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Reaction Steps

To a mixture of 3-(4-fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid (125 mg, 0.488 mmol) and Et3N (0.400 mL, 2.88 mmol) in DMF (3 mL) is added benzotriazol-1-yloxy)tripyrrolidinophosphoniumhexafluorophosphate (PyBOP) (0.300 g, 0.577 mmol). After 10 minutes, C-(2-bromopyridin-4-yl)-methylamine di-hydrochloride salt (153 mg, 0.589 mmol) is added and the mixture is stirred at room temperature. After 2 hours, the mixture is diluted with saturated aqueous ammonium chloride (10 mL) and extracted with EtOAc (3×7 mL). The combined organic layers are washed with saturated aqueous ammonium chloride (2×10 mL), brine (2×10 mL), dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0-2% methanol in dichloromethane. The resulting solid is triturated with ethyl ether to afford the title compound.

Provenance & Evidence