Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Diethyl (cyanomethyl)phosphonate | HCID 75676 | — |
| Reactant | HCID 59334563 | HCID 59334563 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ammonium Chloride | HCID 25517 | — |
| Product | HCID 59334588 | HCID 59334588 | 86.4% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08110585B2 |
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| Source dataset | uspto-grants-2012_02 |
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| ORD ID | ord-f8eec64496ef4aa78d322f36d908b7f9 |
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| Source note | uspto-grants-2012_02 |
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