Chloroform → HCID 58608117, compound

Participants

Reaction Steps

A 100-ml round bottomed flask equipped with a reflux condenser fitted with a nitrogen inlet adapter was charged with 7-benzyl-2-iodo-3-phenylfuro[2,3-b]pyridin-4(7H)-one 4f (3.08 g, 3.46 mmol) and chloroform (35 mL). Oxalyl chloride (1.76 g, 1.21 mL, 13.84 mmol) and N,N-dimethylformamide (0.20 mL) were added, and the reaction was heated at reflux for 18 h. The reaction mixture was concentrated, and the residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a black oil. Purification via column chromatography on silica gel (gradient elution with 0-25% ethyl acetate-hexane) afforded 4-chloro-2-iodo-3-phenylfuro[2,3-b]pyridine 6d as a brown oil. MS (MH+) 356.0; Calculated 355 for C13H7ClINO.

Provenance & Evidence