5-Bromo-4-methylpyridine-3-carbonitrile → 5-Ethenyl-4-methylpyridine-3-carbonitrile
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas refluxed under Ar for 4 hours
- concentrationConcentrated
- 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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