Chlorodifluoromethane → 8-Difluoromethoxy-3-iodo-2-phenyl-pyrano[2,3-c]pyridin-4-one

Participants

Reaction Conditions

Reaction Steps

Chlorodifluoromethane was bubbled into a solution of 3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione (100 mg, 0.27 mmol) and potassium carbonate (55 mg, 0.40 mmol) in DMF (3.0 mL) over 2 min. The reaction mixture was stirred at 40° C., for 2 days under a chlorodifluoromethane balloon. The resulting mixture was partitioned between ethyl acetate (40 mL) and water (20 mL) and the phases were separated. The organic layer was washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was subjected to flash chromatography (SiO2, 20% ethyl acetate in cyclohexane) to give the title compound as a white solid (33 mg, 29%). LCMS (Method B): RT=4.46 min, [M+H]+=416.

Provenance & Evidence