Imidazo(1,2-a)pyridine → 3-Iodoimidazo[1,2-a]pyridine

Participants

Reaction Steps

In a 1 L three-necked flask, imidazo[1,2-a]pyridine (4.1 g, 34.7 mmol), in THF was treated with butyllithium (14.6 ml, 36.4 mmol) at −50° C. N-iodosuccinimide (8.59 g, 38.2 mmol) in 50 ml THF and added slowly and temp allowed to rise to 0° C. This was diluted with water and hexane. The organic layer was washed with 10% brine/water (2×), dried (MgSO4) and evaporated to give a solid. The solid was dissolved in THF/DCM and purified by flash chromatography (80-100% ethyl acetate/hexane) to give the desired isomer 3-iodoimidazo[1,2-a]pyridine. 1H NMR (300 MHz, DMSO-d6) δ: 8.32 (m, 1H) 7.72 (s, 1H) 7.62 (m, 1H) 7.34 (m, 1H) 7.06 (t, 1H).

Provenance & Evidence