Methanol → Methyl imidazo[1,2-a]pyridine-8-carboxylate

Participants

Reaction Steps

To a stirred solution of imidazo[1,2-a]pyridine-8-carboxylic acid (3.8 g, 23 mmol) in methanol (100 mL) is added thionylchloride (8.36 g, 70.3 mmol) and the mixture is warmed at reflux. After 8 hours, the reaction mixture is cooled to room temperature and quenched with saturated aqueous NaHCO3, and extracted with EtOAc (3×250 mL). The combined organic layers are washed with water, brine, dried over Na2SO4 and concentrated. The crude material is purified by silica gel chromatography eluting with 3% MeOH in CH2Cl2 to afford imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester. Mp: 71-73° C.

Provenance & Evidence