Triphenylphosphine → 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine

Participants

Reaction Steps

To a solution of 6-nitrofuro[3,2-c]pyridin-7-ol (Intermediate 7) (2.10 g, 11.6 mmol) and (S)-1-(2,6-dichloro-3-fluorophenyl)-ethanol (2.68 g, 12.8 mmol, prepared according to literature procedures: WO2006/021881A2) in THF (30 mL) were added PPh3 (4.31 g, 16.4 mmol) and diisopropyl azodicarboxylate (3.32 g, 16.4 mmol) at 0° C. After 10 min, the cold-bath was removed and the resulting mixture was stirred at rt overnight. LC-MS showed completion of the reaction. The reaction mixture was evaporated under vacuum to give an oil, which was purified by silica gel flash chromatography (DCM:Hexanes=2:1) to afford 4.2 g of the desired product as a light-yellow oil (yield: 97%). 1H NMR (CDCl3, 400 MHz): δ=1.94 (d, J=6.8 Hz, 3H), 6.69 (q, J=6.8 Hz, 1H), 6.93 (d, J=2.3 Hz, 1H), 7.05 (t, J=8.3 Hz, 1H), 7.27 (dd, J=8.8, 4.8 Hz, 1H), 7.78 (d, J=2.3 Hz, 1H), 8.42 (s, 1H).

Provenance & Evidence