Water → 1-Methyl-1H-pyrrolo[2,3-B]pyridine-5-carbonitrile

HRID 40724Notes

Reaction equation

HRID 40724 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]#[N:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].I[CH3:15].O>CN(C=O)C>[CH3:15][N:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]#[N:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117883551H-Pyrrolo[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 497588931-Methyl-1H-pyrrolo[2,3-B]pyridine-5-carbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile (2.88 g, 20.1 mmol) in DMF (40 mL) was added 60% NaH (2.41 g, 60.4 mmol). After 20 minutes, iodomethane was added in one portion (6.3 mL, 101 mmol) and the resulting mixture was stirred overnight. The following day, water was carefully added drop-wise to quench the remaining NaH before additional water was added (50 mL) causing precipitation of the product. Filtration and drying in vacuo afforded 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (3.16 g, 20.1 mmol, 100% yield) which was subsequently used without further purification. ES MS (M+H+)=158.

Workup

  1. customto quench the remaining NaH before additional water
  2. additionwas added (50 mL)
  3. customprecipitation of the product
  4. filtrationFiltration
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-4c76bac121d84719845ec22f57e7a228
Source dataset
uspto-grants-2013_09
Patent number
US08530483B2

Reaction notes

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