p-Fluoronitrobenzene → HCID 44609574, compound

Under ice-cooling, 2-aminocarbonylamino-6-hydroxyindole-3-carboxamide (Compound No.2-1, 1.3 g, 5.5 mmol) in anhydrous N,N-dimethylformamide (7 mL) was added dropwise to a suspension of 60% sodium hydride (450 mg, 11 mmol) in anhydrous N,N-dimethylformamide (15 mL) over a period of 5 minutes and the mixture was stirred for 5 minutes. Moreover 4-fluoronitrobenzene (640 μL, 6.0 mmol) was added thereto, and the mixture was stirred for 15 minutes at room temperature and stirred overnight at 60° C. After cooling, the reaction solution was diluted with water (300 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (200 mL) and brine (200 mL), and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained solid was filtered off and washed with a mixed solvent of chloroform-diethyl ether solution (1:2, 60 mL). The solid was dried at 40° C. for 1 hour under reduced pressure to give the title compound (1.2 g) as a brown solid (59%).

1. temperatureUnder ice-cooling
2. stirringthe mixture was stirred for 15 minutes at room temperature
3. stirringstirred overnight at 60° C
4. temperatureAfter cooling
5. extractionextracted with ethyl acetate (200 mL)
6. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate (200 mL) and brine (200 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. customThe solvent was removed under reduced pressure
9. filtrationthe obtained solid was filtered off
10. washwashed with a mixed solvent of chloroform-diethyl ether solution (1:2, 60 mL)
11. customThe solid was dried at 40° C. for 1 hour under reduced pressure

ORD record

ord-56662404e2bd48d3ac4de792cfe1241d

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445529B2