Sodium hydride → HCID 59334588, compound

Temperature

0 °C

To a solution of diethyl cyanomethylphosphonate (1.62 mL, 10.02 mmol) in tetrahydrofuran (70 mL) was added 60% sodium hydride (370 mg, 9.25 mmol) under ice-cooling, and the mixture was stirred at 0° C. for 30 min. To the mixture was added a solution of 7-chloro-2-methyl-2H-indazole-4-carbaldehyde (1.50 g, 7.71 mmol) in tetrahydrofuran (30 mL) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction solution was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85→40/60) to give the title compound (1.45 g, yield 86%).

1. temperaturecooling
2. temperaturecooling
3. stirringthe mixture was stirred at room temperature for 1 hr
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85→40/60)

ORD record

ord-f8eec64496ef4aa78d322f36d908b7f9

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110585B2