Nitrogen → HCID 22624322, compound

Participants

Reaction Conditions

Reaction Steps

To a 125 mL three-necked round-bottomed flask equipped with septum, condenser and N2 inlet were added 2.4 mL (26.2 mmol) 2-butanol and 20 mL dry dimethylformamide. The solution was heated to 80° C., and 1.2 g (60% in oil, 30 mmol) sodium hydride was added. The reaction was heated at 80° C. with bubbling for 1 hour, then a solution of 2.5 g (8.7 mmol) N-t-butylcarbonyl-6-(2-fluoro-4-methylphenyl)-pyridin-2-ylamine in 20 mL dry dimethylformamide was added, and the reaction heated at 80° C. for 24 hours. The reaction was cooled, poured into water, and extracted into ethyl acetate. The organic layer was washed thoroughly with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluant to afford 2.4 g (75%) of the product as an oil.

Provenance & Evidence