Phosphorus oxychloride → HCID 58608149, compound

Participants

Reaction Conditions

Reaction Steps

A resealable tube was charged with 7-benzyl-2-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-phenyl-7H-furo[2,3-b]pyridin-4-one (4c) (0.100 g, 0.197 mmol) and phosphorous oxychloride (2.0 mL). The system was flushed with argon and the tube was sealed. The mixture stirred at 110° C. for 1.5 h. The reaction mixture was concentrated, and the residue was partitioned between dichloromethane and ice water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, and concentrated to afford an orange brown oil. This oil was purified via preparative thin layer chromatography (eluting with 90:10:1, dichloromethane/methanol/ammonium hydroxide) to afford 4-chloro-2-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-phenyl-furo[2,3-b]pyridine 6c as an off white solid. MS (MH+) 435.0; Calculated 434 for C25H23ClN2O3.

Provenance & Evidence