2-Aminopyridine → Ethyl imidazo[1,2-a]pyridine-2-carboxylate

Participants

Reaction Steps

A solution of 2-aminopyridine (5.0 g, 53.2 mmol) in THF (150 mL) was treated with ethyl bromopyruvate (10.32 g, 57.0 mmol) at room temperature followed by heating the mixture at reflux for 16 h. The resulting white precipitate was collected by filtration and washed with THF (10 mL). Recrystallization of the solids from boiling EtOH (20 mL) gave ethyl imidazo[1,2-a]pyridine-2-carboxylate (6.10 g, 60% yield). ESI MS: m/z 191 [M+1]+. See, e.g., J. Med. Chem., 2003, 46, 3914-29.

Provenance & Evidence