Methyl iodide → 1-methyl-1H-indole-5-carbonitrile

HRID 475293Notes

Reaction equation

HRID 475293 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].I[CH3:15]>CN(C=O)C>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27513Indole-5-carbonitrile

Product 1

HCID 114125131-methyl-1H-indole-5-carbonitrileYield 122%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-indole-5-carbonitrile (600 mg, 4.2 mmol) in DMF (5 mL) at 0° C. was added NaH (201 mg, 60% in oil, 8.4 mmol) with vigorous stirring. The solution was stirred 30 min, then iodomethane (1.8 g, 12.6 mmol) was added. The reaction mixture was stirred at RT for 4 h. The reaction was quenched with water (50 mL) and extracted with EtOAc (3×100 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated under reduced pressure to afford 800 mg of 1-methyl-1H-indole-5-carbonitrile (294) as white solid: MS (ESI) m/z=157.3 [M+1]+.

Workup

  1. stirringThe reaction mixture was stirred at RT for 4 h
  2. customThe reaction was quenched with water (50 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b74348e67d4b4929bc5ded159c2803ad
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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