1,2-Dibromoethane → 1-(Pyrazin-2-YL)cyclopropanecarbonitrile

HRID 931156노트

반응식

HRID 931156 반응식
[H-].[Na+].[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].Br[CH2:13][CH2:14]Br>CN(C)C=O>[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1([C:10]#[N:11])[CH2:14][CH2:13]1

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 12782906(Pyrazin-2-yl)acetonitrile

생성물 1

HCID 584311071-(Pyrazin-2-YL)cyclopropanecarbonitrile수율 31.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of sodium hydride (0.386 g, 16.1 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added dropwise a solution of 2-(pyrazin-2-yl)acetonitrile (0.55 g, 4.6 mmol) and 1,2-dibromoethane (2.25 g, 11.9 mmol) in anhydrous N,N-dimethylformamide (8 mL) over a period of 10 min at room temperature. The mixture was stirred for 18 h, then was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 100% dichloromethane) to afford 1-(pyrazin-2-yl)cyclopropanecarbonitrile (210 mg, 31%).

후처리

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via column chromatography (100-200 mesh silica gel, 100% dichloromethane)

출처 및 근거

ORD 기록
ord-035158bd72094f139941edfd772382ab
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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