Tributylvinyltin → HCID 17877573, compound

HRID 556430Notes

Reaction equation

HRID 556430 reaction equation
Br[C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.[CH2:11]([Sn](CCCC)(CCCC)C=C)[CH2:12]CC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:11]([C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2)=[CH2:12]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 185216472-Bromo-1H-imidazo[4,5-b]pyridine

Product 1

HCID 17877573HCID 17877573, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of bromoimidazo[4,5-b]pyridine (1 eq.), tributyl(vinyl)tin (1.5-3 eq.), and tetrakis(triphenylphosphine)palladium(0) (0.1 eq.) in toluene (deoxygenated with N2, 20 ml/mmol ml) is stirred under reflux for 4 h. Concentration in vacuo and chromatographic purification (EtOAc/hexane gradient) yields the corresponding vinylimidazo[4,5-b]pyridine.

Workup

  1. temperatureunder reflux for 4 h
  2. concentrationConcentration
  3. customin vacuo and chromatographic purification (EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-6c2755fd12534cb6bf5940d3664a6fc6
Source dataset
uspto-grants-2011_11
Patent number
US08058289B2

Reaction notes

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