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

HRID 40724ノート

反応式

HRID 40724 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4c76bac121d84719845ec22f57e7a228
出典データセット
uspto-grants-2013_09
特許番号
US08530483B2

反応ノート

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