5-Bromoindole → Indole-5-carbonitrile

HRID 641875Notes

Reaction equation

HRID 641875 reaction equation
[C:1]([Cu])#[N:2].Br[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2>CN1CCCC1=O>[NH:10]1[C:11]2[C:7](=[CH:6][C:5]([C:1]#[N:2])=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

4

Reactant 2

HCID 249055-BromoindoleHCID 178418546HCID 178418546, compound

Product 1

HCID 27513Indole-5-carbonitrileYield 103%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

CuCN (3.7 g, 40.70 mmol) was added to a solution of 5-bromo-1H-indole (5 g, 25.26 mmol) in 1-methylpyrrolidin-2-one (25 mL), and the resulting solution was stirred at reflux for 18 hours. The reaction mixture was then added to 200 g of ice and the mixture was filtered. The filter cake was washed with ammonium hydroxide (3×50 mL). The residue was dissolved in chloroform (600 mL) and then filtered. The organic layer was washed with water (200 mL), and dried (MgSO4). After a further filtration, the filtrate was concentrated to yield 3.7 g (82%) of 1H-indole-5-carbonitrile as brown oil.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationthe mixture was filtered
  3. washThe filter cake was washed with ammonium hydroxide (3×50 mL)
  4. dissolutionThe residue was dissolved in chloroform (600 mL)
  5. filtrationfiltered
  6. washThe organic layer was washed with water (200 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationAfter a further filtration
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0595045c329042d7b4f039ada9af541a
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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