Acetic Acid → (R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

Participants

Reaction Steps

To a stirred mixture of AcOH (150 mL) and EtOH (150 mL) was suspended 5-bromo-3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-2-nitropyridine (6.6 g, 0.016 mol) and iron chips (8.8 g, 0.16 mol). The reaction was heated slowly to reflux and allowed to stir for 1 hour. The reaction was cooled to room temperature then diethyl ether (100 mL) and water (100 mL) was added. The solution was carefully neutralized by the addition of sodium carbonate. The combined organic extracts were washed with saturated NaHCO3 (2×100 mL), H2O (2×100 mL) and brine (1×100 mL) then dried over Na2SO4, filtered and concentrated to dryness under vacuum to yield the title compound as a white solid (5.0 g, 84%).

Provenance & Evidence