Water → 5-cyano-N-(4-methoxybenzyl)-3-methylindazole

HRID 490091Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[N:6]=[C:5]2[CH3:20].[C-:21]#[N:22].[Na+].C(OCC)(=O)C.O>CN1C(=O)CCC1.[Cl-].[Na+].O.[Ni](Br)Br>[C:21]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[N:6]=[C:5]2[CH3:20])#[N:22]

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of 5-bromo-N-(4-methoxybenzyl)-3-methylindazole 105 (0.12 g, 0.363 mmol) in NMP (N-methylpyrrolidinone; 2 mL) was added sodium cyanide (0.035 g, 0.714 mmol) and nickel bromide (0.079 g, 0.362 mmol). The reaction mixture was heated in a microwave reactor at 180° C. for 20 minutes. Ethyl acetate (100 mL) was added and the organic layer was washer 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-N-(4-methoxybenzyl)-3-methylindazole 106 (0.1 g, 0.361 mmol).

Workup

dry with materialThe organic layer was dried over sodium sulfate
customThe organic solvent was evaporated under reduced pressure
customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record: ord-a3228b1610b64aa3881d2ef461f1f1f5
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528132B2

Reaction notes

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