Pyridine → 3-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-isonicotinic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl-3-aminopyridine-4-carboxylate hydrochloride (1.0 g, 4.93 mmol) and pyridine (1.2 ml, 14.8 mmol) in toluene (10 ml) at room temperature under argon was added 20% phosgene in toluene (3.7 ml, 7.15 mmol) and the mixture was heated at 90° C. for 1 h. The mixture was filtered, and the filtrate was concentrated to dryness. The crude material was dissolved in toluene (10 ml), (5-phenyl-benzofuran-2-yl)-methanol (0.922 g, 4.11 mmol) and DMAP (0.05 g, 0.411 mmol) were added and the mixture was heated at 90° C. for 18 h. The solvent was evaporated to dryness. Purification by chromatography gave 0.538 g of 3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-isonicotinic acid ethyl ester as a white solid.

Provenance & Evidence