Bromine → 3-Bromoimidazo(1,2-a)pyrazine

Participants

Reaction Conditions

Reaction Steps

Imidazo[1,2-a]pyrazine (1.191 g, 10 mmol, Intermediate 1) and sodium acetate (0.984 g, 12.00 mmol) were suspended in methanol (10 ml) saturated with potassium bromide (excess) and cooled to −10° C. Bromine (0.515 mL, 10.00 mmol) was added dropwise and the mixture stirred at −10° C. for 10 min. The solution was quenched by the addition of 1N sodium sulfite solution (10 ml) and concentrated in vacuo. The residue was partitioned between ethyl acetate (100 ml) and 50% saturated sodium bicarbonate solution (100 ml). The aqueous phase was extracted with ethyl acetate (2×100 ml), combined, washed with brine (50 ml), dried over anhydrous sodium sulfate and concentrated to give crude 3-bromoimidazo[1,2-a]pyrazine (1.66 g, 8.38 mmol, 84% yield) that was used in subsequent steps without further purification 3-bromoimidazo[1,2-a]pyrazine (1.66 g, 8.38 mmol, 84% yield).

Provenance & Evidence