Tri(butyl)vinyltin → 1-{4-Nitro-2-[(1E)-prop-1-en-1-yl]phenyl}-3-vinylpyridin-2(1H)-one

HRID 452235Notes

Reaction equation

HRID 452235 reaction equation
Br[C:2]1[C:3](=[O:20])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2/[CH:17]=[CH:18]/[CH3:19])[CH:5]=[CH:6][CH:7]=1.[CH2:21](C([Sn])=C(CCCC)CCCC)[CH2:22]CC>O1CCOCC1.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>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH:21]=[CH2:22])[C:3]2=[O:20])=[C:9](/[CH:17]=[CH:18]/[CH3:19])[CH:10]=1)([O-:16])=[O:15]

Participants

5

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 595366023-Bromo-1-{4-nitro-2-[(1E)-prop-1-en-1-yl]phenyl}pyridin-2(1H)-one

Product 1

HCID 595366061-{4-Nitro-2-[(1E)-prop-1-en-1-yl]phenyl}-3-vinylpyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

929 mg (2.77 mmol) of the compound from Example 44A are dissolved in 14 ml of anhydrous dioxane, and 64 mg (0.06 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. At room temperature, 1.06 g (3.33 mmol) of tributylvinyl tin are added slowly, and, after the addition has ended, the mixture is heated at reflux for 21 h. The reaction solution is allowed to cool and is filtered through kieselguhr. The filter cake is then washed with ethyl acetate, and the combined organic filtrates are concentrated to dryness under reduced pressure. The product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate=4:1). This gives 568 mg (70% of theory) of the desired product.

Workup

  1. additionafter the addition
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 21 h
  4. temperatureto cool
  5. filtrationis filtered through kieselguhr
  6. washThe filter cake is then washed with ethyl acetate
  7. concentrationthe combined organic filtrates are concentrated to dryness under reduced pressure
  8. customThe product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-aecc5967a9a8404b803d2a744469ff20
Source dataset
uspto-grants-2013_07
Patent number
US08487111B2

Reaction notes

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