Ethyl bromopyruvate → Ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 2-amino-5-chloropyridine (2.0 g, 16 mmol) [Matrix Scientific, 021118] in acetone (39 mL) was treated with ethyl bromopyruvate (2.2 mL, 16 mmol) and heated at 60° C. for 45 min. The reaction mixture was cooled to 20° C. and the suspension was filtered. The solid that was collected was washed with a small amount of cold acetone and dried in vacuo. The solid was diluted with ethanol (12 mL) and water (19 mL), heated at 65° C., and treated with sodium bicarbonate (1.6 g, 19 mmol) portionwise. The reaction mixture was cooled to 20° C. and the suspension was filtered. The solid that was collected was washed with water (4×80 mL) and dried in vacuo to give the desired product (2.6 g, 74%). LCMS for C10H10ClN2O2 (M+H)+: m/z=225.1.

Provenance & Evidence