Methyl iodide → HCID 71547715, compound

Participants

Reaction Steps

To the colorless solution of N-[3-[[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-methyl-carbamoyl]-2-methoxy-phenyl]pyridine-4-carboxamide (example G-16 above) (0.120 g, 0.175 mmole) in N,N-dimethylformamide (5 ml), magnetically stirred under argon atmosphere was added sodium hydride (60% suspension in oil) (0.008 g, 0.192 mmole). After the gas evolution stopped, the resulting yellow solution was treated with iodomethane (0.012 ml, 0.027 g, 0.192 mmole). After 10 minutes, two drops of methanol was added and the reaction mixture was evaporated under reduced pressure. The residue was taken up in dichloromethane (5 ml) and water (10 ml). After phase separation, the aqueous solution was extracted twice with dichloromethane. The organic extracts were dried over sodium sulfate and evaporated. The residue was purified on a silica gel column using a gradient of ethyl acetate 20%-cyclohexane 80% to ethyl acetate 60%-cyclohexane 40%. The title product was a pale yellow oil showing, by LC-MS analysis (method 6 described hereunder) a retention time of 1.09 min and a M+H+ mass peak of 700.

Provenance & Evidence