Ethyl Acetate → HCID 86658479, compound

Participants

Reaction Steps

Pyridinium p-toluene-sulfonate (2.53 g, 10.06 mmol) was added to a solution of 7-bromo-3-chloro-9-fluoro-5-methyl-5H-chromeno[2,3-c]pyridin-5-ol (3.15 g, 9.14 mmol) in DCE (91 mL) at 55° C. The reaction was stirred 2.5 hours at which time TLC analysis (10:1 Hex/EtOAc) showed the reaction to be complete. The reaction was poured into saturated aqueous sodium bicarbonate (150 mL) and the layers were separated. The aqueous layer was extracted with CH2Cl2 (4×150 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude product 7-bromo-3-chloro-9-fluoro-5-methylene-5H-chromeno[2,3-c]pyridine which was concentrated and used without further purification. MS m/z=327.9 [M+H].

Provenance & Evidence