Chloroacetaldehyde → Imidazo[1,2-a]pyridine-7-methanol

Participants

Reaction Steps

To a solution of (2-amino-pyridin-4-yl)-methanol (0.40 g, 3.3 mmol) in EtOH was added NaHCO3 (0.56 g, 6.67 mmol) followed by chloroacetaldehyde (0.81 ml, 5.0 mmol). The mixture was refluxed for 2 h. Solvents were removed in vacuo and the crude mixture was partitioned between water and EtOAc. The aqueous was further extracted with EtOAc, the organics combined, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using silica column chromatography (0-50% MeOH/Et2O) to afford 0.40 g of product MS: [M+H]+=149.

Provenance & Evidence