Tributylvinyltin → HCID 58955123, compound

HRID 1990970Notes

Reaction equation

HRID 1990970 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12].[CH2:20]([Sn](CCCC)(CCCC)C=C)[CH2:21]CC>C1(C)C=CC=CC=1.C(OCC)(=O)C.[F-].[K+].CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[C:14]1([S:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([CH:20]=[CH2:21])[CH:3]=3)[NH:7][CH:6]=2)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 2

HCID 81998TributylvinyltinHCID 58955093HCID 58955093, compound

Product 1

HCID 58955123HCID 58955123, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 178424406HCID 178424406, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 522689Potassium FluorideSolvent

Procedure

5-bromo-3-(phenylsulfonyl)-1H-indole (505 mg, 1.50 mmol) and dichlorobis(tri-o-tolylphosphine)-palladium(II) (118 mg, 0.09 mmol) were dissolved in toluene (5 mL) and stirred for 10 minutes at room temperature under a nitrogen atmosphere. Tributyl(vinyl)tin (619 mg, 1.95 mmol) was added and the mixture was refluxed for 1 hour. The mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), 1 M KF (5 mL) and stirred for 12 hours. The resultant tin salt precipitate is removed by suction filtration and the organic layer was washed with water (5 mL), then brine and dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (40% ethyl acetate/petroleum ether) gave the title compound as a white solid (313 mg, 74%). Mp: 140-145° C. MS (ES+): 284 (M+H).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureThe mixture was cooled to room temperature
  3. stirringstirred for 12 hours
  4. customThe resultant tin salt precipitate is removed by suction filtration
  5. washthe organic layer was washed with water (5 mL)
  6. dry with materialbrine and dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography (40% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-500896f78b7d432ca14d45e2f83f95a0
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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