1,2-Dibromoethane → 1-(Pyrazin-2-yl)cyclopropane-1-carbonitrile

HRID 931156Notes

Reaction equation

HRID 931156 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 584311071-(Pyrazin-2-yl)cyclopropane-1-carbonitrileYield 31.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-035158bd72094f139941edfd772382ab
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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