4-Methylmorpholine → N-[4-[(3,4-dibromophenyl)amino]-3-cyano-6-quinolinyl]-2-butynamide

Participants

Reaction Conditions

Reaction Steps

Isobutyl chloroformate (0.984 g, 7.18 mmol) and N-methylmorpholine (0.725 g, 7.18 mmol) were added to an ice cold solution of 0.604 g (7.18 mmol) of 2-butynoic acid in 25 mL of tetrahydrofuran. After 10min, a solution of 1.20 g (2.87 mmol) of 6-amino-4-[(3,4-dibromophenyl)amino]-3-quinolinecarbonitrile in 12 mL of tetrahydrofuran was added dropwise. After stirring overnight at 25° C., volatile material was removed and the residue was slurried in water and filtered. The crude product was washed with boiling EtOAC and ethanol and dried in vacuo(50° C.) to give 0.651 g of brown solid: mass spectrum (electrospray, m/e): M+H 485.

Provenance & Evidence