Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | HCID 59334491 | HCID 59334491 | — |
| Catalyst | Nickel(II) bromide | HCID 278492 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 59334572 | HCID 59334572 | 31.2% |
Reaction Steps
To a solution of N-{[2-(5-bromo-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide (200 mg, 0.621 mmol) obtained in Example 29 in N-methylpyrrolidinone (3 mL) were added nickel(II) bromide (136 mg, 0.621 mmol) and sodium cyanide (61 mg, 1.241 mmol), and the mixture was stirred at 180° C. for 40 min using microwave. The reaction solution was diluted with ethyl acetate, washed with water and 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 (methanol/ethyl acetate=0/100→5/95) and recrystallization (ethyl acetate/hexane) to give the title compound (52 mg, yield 31%).
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-23323cdae47c4b4dad84436e440d95d4 |
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| Source note | uspto-grants-2012_02 |
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