Bromine → 3-Bromo-7-methoxyimidazo[1,2-a]pyridine

Participants

Reaction Conditions

Reaction Steps

7-Methoxyimidazo[1,2-α]pyridine (1.0 g, 6.8 mmol) and sodium acetate (0.67 g, 8.1 mmol) were dissolved in a saturated solution of potassium bromide in methanol (5 ml) and cooled to 0° C. before adding bromine (1.13 g, 7.1 mmol) dropwise over 5 min. The mixture was allowed to stir for 15 min before pouring onto saturated sodium hydrogencarbonate solution (50 ml). The resulting yellow solid was collected by filtration and dried. This solid was purified by flash column chromatography on silica eluting with 50% ethyl acetate in isohexane to afford 3-bromo-7-methoxyimidazo[1,2-α]pyridine (0.4 g, 26%) as a white solid. 1H NMR (360 MHz, CDCl3) δH 3.87 (3H, s), 6.64 (1H, dd, J 2 and 7), 6.88 (1H, d, J 2), 7.45 (1H, s), 7.92 (1H, d, J 7).

Provenance & Evidence