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

Participants

Reaction Conditions

Reaction Steps

Alternate synthesis: To a solution of Methanesulfonic acid (S)-1-(2,6-dichloro-3-fluorophenyl)-ethyl ester (109 mg, 0.380 mmol) and 6-nitrofuro[3,2-c]pyridin-7-ol (68.4 mg, 0.380 mmol) in DMF (1.0 mL) was added potassium carbonate (57.2 mg, 0.414 mmol), and the resulting suspension was stirred at ambient temperature for 1 h and at 60° C. overnight. Methanesulfonic acid (S)-1-(2,6-dichloro-3-fluorophenyl)ethyl ester (32.7 mg, 0.114 mmol) and potassium carbonate (16 mg, 0.12 mmol) were added to the reaction mixture, and the mixture was heated at 70° C. for 3 days. Water and EtOAc were added to the reaction mixture, the layers were separated, and the aqueous layer was extracted with EtOAc (3×15 mL). The combined EtOAc extracts were washed with 1N NaOH (2×), water (2×), and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound.

Provenance & Evidence