5-Bromo-4-methylpyridine-3-carbonitrile → 5-Ethenyl-4-methylpyridine-3-carbonitrile

HRID 1502032Notes

Reaction equation

HRID 1502032 reaction equation
Br[C:2]1[C:3]([CH3:10])=[C:4]([C:8]#[N:9])[CH:5]=[N:6][CH:7]=1.[CH:11]([B-](F)(F)F)=[CH2:12].[K+]>CCO>[CH:11]([C:2]1[C:3]([CH3:10])=[C:4]([C:8]#[N:9])[CH:5]=[N:6][CH:7]=1)=[CH2:12]

Participants

4

Reactant 2

HCID 70606815-Bromo-4-methylpyridine-3-carbonitrileHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 139439175-Ethenyl-4-methylpyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-bromo-4-methylpyridine-3-carbonitrile (4.40 g, 22.3 mmol), potassium vinyltrifluoroborate (3.70 g, 27.9 mmol) and Pd (dppf)2Cl2 (0.4 g) in 30 mL of EtOH and 30 mL of TEA was refluxed under Ar for 4 hours. Concentrated, the residue was purified by column chromatography (petrol ether: EtOAc=50:1) to afford 5-ethenyl-4-methylpyridine-3-carbonitrile.

Workup

  1. temperaturewas refluxed under Ar for 4 hours
  2. concentrationConcentrated
  3. customthe residue was purified by column chromatography (petrol ether: EtOAc=50:1)

Sources & evidence

ORD record
ord-7445b1458bd54f859535ba0994ba61c8
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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