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

HRID 445138Notes

Reaction equation

HRID 445138 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-ef4eb52ca38b4c9fab16b051cae6d78a
Source dataset
uspto-grants-2013_07
Patent number
US08476293B2

Reaction notes

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