N-Iodosuccinimide → Methyl 3-iodoimidazo[1,2-a]pyridine-8-carboxylate

Participants

Reaction Steps

A mixture of imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester (3.24 g, 18.3 mmol) and N-iodosuccinimide (NIS) (4.11 g, 18.3 mmol) in acetonitrile (50 mL) is stirred at room temperature. After 2 hours, the reaction mixture is quenched with saturated aqueous Na2S2O3 and extracted with EtOAc (3×100 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 80% EtOAc in hexanes to afford 3-iodo-imidazo[1,2-a]pyridine-8-carboxylic acid methyl ester. Mp: 99-110° C.

Provenance & Evidence