Acetic Acid → Ethyl 3-(hydroxymethyl)imidazo[1,2-a]pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 570 mg (3.0 mmol) ethyl imidazolo[1,2-a]pyridine-2-carboxylate, glacial acetic acid (0.8 mL) and 1 g (12 mmol) sodium acetate is treated with 6 mL 37% formaldehyde in water. The mixture is heated in a sealed tube at 90° C. for 6 hr and the acetic acid removed in vacuo. The residue is made basic by addition of 2M sodium hydroxide and extracted into 3×10 mL dichloromethane containing 1% methanol. The organic extract is dried over anhydrous MgSO4 and the solvent removed in vacuo to give the crude residue. The residue is flash chromatographed with initially 10% methanol in dichloromethane to afford 325 mg (49%) ethyl 3-(hydroxymethyl)-imidazolo[1,2-a]pyridine-2-carboxylate.

Provenance & Evidence