Benzyl Bromide → 1-Benzyl-3-cyanoindazole

HRID 990812

Reaction equation

HRID 990812 reaction equation
[H-].[Na+].[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1)#[N:4].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:3]#[N:4])=[N:6]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 4375561H-Indazole-3-carbonitrile

Product 1

HCID 158403551-Benzyl-3-cyanoindazoleYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

420 mg of NaH (60% in oil, 10.3 mmol) were added in portions to 1.0 g of 3-cyanoindazole (7.0 mmol) and 1.7 ml of benzyl bromide (14.0 mmol) in 6 ml of THF, and the mixture was stirred at room temperature for 15 hours. The reaction was quenched with 2 drops of water, the mixture was concentrated and the residue was chromatographed (SiO2; petroleum ether:ethyl acetate 3:1). 1.3 g of a solid were obtained.

Workup

  1. customThe reaction was quenched with 2 drops of water
  2. concentrationthe mixture was concentrated
  3. customthe residue was chromatographed (SiO2; petroleum ether:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-84589dce0ecf4401b325779aba1334ac
Source dataset
uspto-grants-2002_10
Patent number
US06462068B1

Linked notes

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