2-Chloro-3,5-dimethylpyrazine → 2-Ethenyl-3,5-dimethylpyrazine

HRID 591502Notes

Reaction equation

HRID 591502 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[N:6][C:5]([CH3:9])=[CH:4][N:3]=1.[CH:10]([B-](F)(F)F)=[CH2:11].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CCO>[CH3:8][C:7]1[C:2]([CH:10]=[CH2:11])=[N:3][CH:4]=[C:5]([CH3:9])[N:6]=1

Participants

5

Reactant 2

HCID 116726802-Chloro-3,5-dimethylpyrazineHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 64292682-Ethenyl-3,5-dimethylpyrazine

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2-chloro-3,5-dimethylpyrazine (2 g) and EtOH (20 mL) were added potassium vinyltrifluoroborate (2.067 g) and TEA (2.93 mL) at room temperature, and the mixture was stirred under nitrogen atmosphere. To the mixture was added PdCl2(dppf) (1.026 g), and the mixture was refluxed for 2 h.

Workup

  1. temperaturethe mixture was refluxed for 2 h.

Sources & evidence

ORD record
ord-80f9858156f349028a806eff8d73f561
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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