Trimethylsilyldiazomethane → 6-bromo-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid methyl ester

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Reaction Steps

To a solution of 6-bromo-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (1.00 equivalent) in THF-MeOH at 0° C. is added TMSCHN2 (1.30 equivalents, 2 M solution in hexanes). The resulting mixture is warmed to room temperature and stirred for 2 hours. The reaction is quenched with AcOH. The reaction mixture is diluted with EtOAc. The organic layer is washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product that is used directly without further purification.

Provenance & Evidence