Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | HCID 59262248 | HCID 59262248 | — |
| Catalyst | Nickel(II) bromide | HCID 278492 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 68997699 | HCID 68997699 | — |
Reaction Steps
To a solution of 5-bromo-3-methyl-N-(2-trimethylsilanylethoxymethyl)indazole 116 (0.5 g, 1.466 mmol) in NMP (10 mL) was added nickel bromide (0.321 g, 1.469 mmol) and sodium cyanide (0.144 g, 2.939 mmol). The reaction mixture was heated in a microwave reactor at 180° C. for 30 minutes. Ethyl acetate (100 mL) was added. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to yield the desired 5-cyano-3-methyl-N-(2-trimethylsilanylethoxymethyl)indazole 117. (0.36 g, 1.254 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07528132B2 |
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| Source dataset | uspto-grants-2009_05 |
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| ORD ID | ord-90821c17fa164d5d8187c20db265c5c9 |
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| Source note | uspto-grants-2009_05 |
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