Tributylvinyltin → HCID 23445130, compound

HRID 433618Notes

Reaction equation

HRID 433618 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH:15]([Sn](CCCC)(CCCC)CCCC)=[CH2:16]>CN(C=O)C.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:15]([C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1)=[CH2:16]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 23445001HCID 23445001, compound

Product 1

HCID 23445130HCID 23445130, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Under an Ar atmosphere, a solution of [1-(3-bromo-phenyl)-1H-imidazol-4-yl]-methanol (3.0 g, 12 mmol) in DMF (90 ml) was successively treated with PdCl2(PPh3)2 (0.87 g, 0.1 mmol) and vinyltributylstannane (4.1 g, 13 mmol). The resulting mixture was heated to 60° C. for 8 h. After evaporation of the solvent the residue was stirred for 30 min with AcOEt (60 ml) and aqueous 10% KF solution. The organic phase was separated and the aqueous phase was extracted 3 times with AcOEt. The combined organic phases were dried (Na2SO4), concentrated and chromatographed [silica, elution with gradient CH2Cl2 to 40% (CH2Cl2/MeOH=9:1)] to yield the title compound as a colorless oil (1.2 g, 51%). MS: m/e=201 (M+H+).

Workup

  1. customAfter evaporation of the solvent the residue
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted 3 times with AcOEt
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated
  6. customchromatographed
  7. wash[silica, elution with gradient CH2Cl2 to 40% (CH2Cl2/MeOH=9:1)]

Sources & evidence

ORD record
ord-917c8c3fd717491b912842b4091d398c
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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