Dimethylformamide → N-(2,4-difluorophenyl)-8-formyl-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To the solution of 8-bromo-N-(2,4-difluorophenyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide (1.0 g, 2.3 mmol) in tetrahydrofuran (20 mL) at −78° C. was added n-BuLi (2.2 mL, 5.5 mmol, 2.5 M in hexane) under a nitrogen atmosphere. After 3 hr, N,N-dimethylformamide (2 mL) was added. The solution was then warmed to −60° C. After 3 hr, aqueous ammonium chloride solution (1 mL, 10%) was added to the reaction mixture, and the resulting solution was extracted with dichloromethane. The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated to yield crude aldehyde, N-(2,4-difluorophenyl)-8-formyl-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide (800 mg), LCMS (ESI) m/z: 386.

Provenance & Evidence