Tributylvinyltin → 4-Vinylnicotinonitrile

HRID 1830860Notes

Reaction equation

HRID 1830860 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:10]([Sn](CCCC)(CCCC)C=C)[CH2:11]CC>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:10]([C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1)=[CH2:11]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 134111124-Chloro-nicotinonitrile

Product 1

HCID 220497874-VinylnicotinonitrileYield 99.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of compound (20)(1.00 g, 7.21 mmol) in dimethylformamide (15 ml) were added tributyl(vinyl)tin (2.50 ml, 8.65 mmol) and dichlorobis(triphenylphosphine)palladium (0.40 g, 0.58 mmol), and the mixture was stirred at 120° C. under an argon atmosphere for one hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was combined and washed with brine and dried (MgSO4). The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography to give a white powder (0.93 g, 99%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9fa260c092e14f6baff2bda7f83dadc2
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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