Water → 1-(1-Methyl-1h-indol-3-yl)cyclopropane-1-carbonitrile

HRID 1847210Notes

Reaction equation

HRID 1847210 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2([C:13]#[N:14])[CH2:12][CH2:11]2)=[CH:2]1.[H-].[Na+].[CH3:17]I.O>CN(C)C=O>[CH3:17][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2([C:13]#[N:14])[CH2:11][CH2:12]2)=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 153783241-(1h-Indol-3-yl)cyclopropanecarbonitrile

Product 1

HCID 154683771-(1-Methyl-1h-indol-3-yl)cyclopropane-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(1H-indole-3-yl)cyclopropanecarbonitrile (183 mg) was dissolved in N,N-dimethylformamide (2 mL) and sodium hydride (60% in oil, 45 mg) was added under ice cooling, followed by stirring for 5 minutes. To the reaction solution, methyl iodide (0.07 mL) was added, followed by stirring at room temperature for one hour. To the reaction solution, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (parallel separation purification system) to obtain the titled compound having the following physical properties (196 mg).

Workup

  1. stirringby stirring at room temperature for one hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (parallel separation purification system)

Sources & evidence

ORD record
ord-3717ea022e0e48bb90011f3ec7d4b27a
Source dataset
uspto-grants-2015_02
Patent number
US08952158B2

Reaction notes

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