Methanol → 5-Formyl-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of sodium methoxide in methanol (30% w/w, 38 mL, 0.21 mol) was added to a mixture of methyl 5-aminofuran-2-carboxylate (15 g, 0.11 mol) and 2-[(dimethylamino)methylene]-1,3-bis(dimethyliminio)propane bis(tetrafluoroborate)salt (38 g, 0.11 mol) in an oven-dried sealed tube. The resulting mixture was heated at reflux for 1 h, then cooled to 23° C., and diluted carefully with water. The reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 40% ethyl acetate in petroleum ether to give the title compound. 1H NMR (300 MHz, CDCl3): δ 8.50 (d, 1H, J=2.0 Hz), 8.13 (d, 1H, J=2.0 Hz), 7.40 (s, 1H), 5.58 (s, 1H), 3.43 (s, 3H), 3.13 (s, 3H).

Provenance & Evidence