Water → 1-Benzyl-1H-indole-5-carbonitrile

HRID 1361030Notes

Reaction equation

HRID 1361030 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[H-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[CH2:14]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 27513Indole-5-carbonitrile

Product 1

HCID 161146831-Benzyl-1H-indole-5-carbonitrileYield 98.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Cyanoindole (1.0 g, 7.0 mmol) was dissolved in N,N-dimethylformamide (14 mL) and cooled in an ice-water bath. Sodium hydride (0.31 g, 60%, 7.8 mmol) was added, and the resulting suspension was stirred for 30 min. Benzyl chloride (0.85 mL, 0.94 g, 7.4 mmol) was added, and the cooling was discontinued. The stirring was continued for 65 hours at room temperature. Water (150 mL) was added, and the mixture was extracted with ethyl acetate (3×25 mL). The combined organic phases were washed with brine (30 mL) and dried with sodium sulfate (1 hour). Filtration and concentration yielded the crude material. Purification by flash chromatography on silica gel eluting with ethyl acetate/heptanes=1:3 afforded 1.60 g 1-benzyl-1H-indole-5-carbonitrile.

Workup

  1. temperaturecooled in an ice-water bath
  2. waitThe stirring was continued for 65 hours at room temperature
  3. extractionthe mixture was extracted with ethyl acetate (3×25 mL)
  4. washThe combined organic phases were washed with brine (30 mL)
  5. dry with materialdried with sodium sulfate (1 hour)
  6. filtrationFiltration and concentration
  7. customyielded the crude material
  8. customPurification by flash chromatography on silica gel eluting with ethyl acetate/heptanes=1:3

Sources & evidence

ORD record
ord-64f854cb2e3e4171a602c7cf64ebaf36
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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