N-bromobutanimide → HCID 24987222, compound

Participants

Reaction Conditions

Reaction Steps

N-Bromosuccinimide (4.8 g, 27 mmol) was added to a solution of 2-aminocarbonylaminoindole-3-carboxamide (Compound 2-10, 5.9 g, 27 mmol) in anhydrous N,N-dimethylformamide (180 mL) under ice-cooling, and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was poured into ice-water (400 mL) and the whole was extracted with ethyl acetate (500 mL). The organic layer was washed with saturated sodium hydrogen carbonate aqueous solution (200 mL×2), 2 N sodium thiosulfate aqueous solution (200 mL×2), brine (150 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resultant solid was washed with chloroform (40 mL) and dried under reduced pressure to give the title compound (5.4 g) as a slightly brown solid (yield 67%).

Provenance & Evidence