Selenium Dioxide → HCID 84819808, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(2,4-difluorophenylamino)-2-methylnicotinonitrile (350 mg, 1.4 mmol) and selenium dioxide (238 mg, 2.14 mmol) in 1-methoxy-2-(2-methoxyethoxy)ethane (7.00 mL) and 0.2 mL of glacial acetic acid was heated in an oil bath at 120° C. for 10 min. The temperature of the oil bath was slowly warmed to 155° C. in 30 min and stirred at this temperature for 3 h. The reaction mixture was cooled to RT, filtered through a pad of Celite washing with EtOAc, and concentrated. The remaining brown solution was purified on an ISCO 12 g column and the product eluted with 50-80% EtOAc in hexanes to afford 6-(2,4-difluorophenylamino)-2-formylnicotinonitrile in residual amount of 1-methoxy-2-(2-methoxyethoxy)ethane. MS (ESI, pos.ion) m/z: M+1=260.0

Provenance & Evidence