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]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.
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