N-bromobutanimide → HCID 24987222, compound

Temperature

50 °C

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%).

1. temperaturecooling
2. extractionthe whole was extracted with ethyl acetate (500 mL)
3. washThe 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)
4. dry with materialdried over anhydrous magnesium sulfate
5. customAfter the solvent was evaporated under reduced pressure
6. washthe resultant solid was washed with chloroform (40 mL)
7. customdried under reduced pressure

ORD record

ord-31884d20c914448ba8350384d411c6db

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193237B2