Sodium hydride → (5-chloro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-ylidene)acetonitrile

To a suspension of 60% sodium hydride (34.8 mg, 0.870 mmol) in tetrahydrofuran (3 mL) was added diethyl cyanomethylphosphonate (152 μL, 0.94 mmol), and the mixture was stirred at room temperature for 15 min. A suspension of 5-chloro-2-methyl-6,7-dihydrocyclopenta[e]indazol-8(2H)-one (160 mg, 0.725 mmol) in tetrahydrofuran (3 mL) was added thereto, and the mixture was stirred at 50° C. for 4 hr. A solution prepared by adding diethyl cyanomethylphosphonate (152 μL, 0.94 mmol) to a suspension of 60% sodium hydride (34.8 mg, 0.870 mmol) in tetrahydrofuran (3 mL), and stirring the mixture at room temperature for 15 min was added to the reaction solution, and the mixture was further stirred at 50° C. for 4 hr. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with diisopropyl ether to give the title compound (131 mg, yield 74%).

1. additionwas added
2. stirringthe mixture was stirred at 50° C. for 4 hr
3. customA solution prepared
4. stirringstirring the mixture at room temperature for 15 min
5. additionwas added to the reaction solution
6. stirringthe mixture was further stirred at 50° C. for 4 hr
7. extractionthe mixture was extracted with ethyl acetate
8. washThe extract was washed with water and saturated brine
9. dry with materialdried over anhydrous sodium sulfate
10. customThe solvent was evaporated under reduced pressure
11. washthe residue was washed with diisopropyl ether

ORD record

ord-d4f86509e20745fb84baca42f7c8ec81

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247429B2