Hydrochloric Acid → 3-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine

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Reaction Steps

To a solution of 3-bromo-7-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine (1.00 g, 2.22 mmol) in EtOH (10 mL) was added iron (0.62 g, 11.1 mmol), followed by 0.1 N aq. HCl (1.1 mL, 0.11 mmol) at 95° C. (bath temp). The resulting mixture was stirred at this temperature for 30 min. Additional 0.1 N aq. HCl (1.1 mL, 0.11 mmol) was added and the mixture was refluxed for another 30 min. TLC and LC-MS showed the reaction was complete. The mixture was diluted with EtOAc (100 mL) and the solid was filtered off through a pad of Celite. The mother liquor was washed with brine (3×25 mL) and dried over anhydrous sodium sulfate. Evaporation of solvents under reduced pressure afforded the title compound as a light-yellow semi-solid (930 mg, 100% yield). 1H NMR (CDCl3, 400 MHz): δ=1.87 (d, J=6.6 Hz, 3H), 5.15 (br s, 2H), 6.55 (q, J=6.6 Hz, 1H), 7.06 (dd, J=9.1, 8.1 Hz, 1H), 7.27 (dd, J=9.1, 5.1 Hz, 1H), 7.44 (s, 1H), 7.96 (s, 1H). MS (ES+): 418.91/420.86/422.89 [MH+].

Provenance & Evidence