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

HRID 40724노트

반응식

HRID 40724 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4c76bac121d84719845ec22f57e7a228
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530483B2

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