Tributylvinyltin → 4-Vinyl-quinoline-6-carbonitrile

HRID 1782007Notes

Reaction equation

HRID 1782007 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH:14]([Sn](CCCC)(CCCC)CCCC)=[CH2:15]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1)=[CH2:15]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 115214964-Bromoquinoline-6-carbonitrile

Product 1

HCID 114920404-Vinyl-quinoline-6-carbonitrileYield 64.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of (c) (1 g, 4.3 mmol) and vinyltributyltin (1.5 mL, 5.17 mmol) in degassed toluene (20 ml) was added tetrakis(triphenylphosphine) palladium (0) (245 mg, 5 mol %) and the mixture was refluxed under argon for 2 hours. Evaporation and flash silica chromatography eluting with chloroform afforded the product as a pale yellow solid (500 mg, 64%).

Workup

  1. temperaturethe mixture was refluxed under argon for 2 hours
  2. customEvaporation and flash silica chromatography
  3. washeluting with chloroform

Sources & evidence

ORD record
ord-3322c82fa1d54539995fdfa8f5ce8b6b
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

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