2-Aminopyridine → Imidazo(1,2-a)pyridine, 2-(p-nitrophenyl)-

Participants

Reaction Steps

A mixture of 2-aminopyridine (0.20 g, 2.11 mmol) and 2-bromo-4′-nitroacetophenone (0.5 g, 2.05 mmol) in EtOH (25 ml) was heated under reflux for 18 h. The reaction mixture was allowed to cool and sodium bicarbonate (88 mg, 1.05 mmol) was added and heating was continued for 2 h. On cooling to room temperature, the solvent was removed under reduced pressure and the residue was dissolved in DCM (40 ml), washed with water (40 ml), and dried (Na2SO4). The solvent was removed under reduced pressure to give a brown solid which was purified by flash chromatography (15:1 DCM/MeOH) to give the title compound (0.27 g, 54%) as a yellow solid.

Provenance & Evidence