Cesium fluoride → 5-Vinylthiophene-3-sulfonic acid[2-(4-fluorophenyl)ethyl]-methyl-amide

HRID 1351299Notes

Reaction equation

HRID 1351299 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][S:11]([C:14]2[CH:18]=[C:17](Cl)[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[CH:20]([Sn](CCCC)(CCCC)CCCC)=[CH2:21].[F-].[Cs+].O1CCOC[CH2:38]1>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:38])[S:11]([C:14]2[CH:18]=[C:17]([CH:20]=[CH2:21])[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 81998TributylvinyltinHCID 866009935-Chlorothiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]amide

Product 1

HCID 210986625-Vinylthiophene-3-sulfonic acid[2-(4-fluorophenyl)ethyl]-methyl-amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-chlorothiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]amide (739 mg), vinyltributyltin (772 mg), cesium fluoride (740 mg), and bis(trit-butylphosphine)palladium (34 mg) in 1,4-dioxane (9 mL) was heated at 100° C. for 16 hours. After the reaction solution was cooled to room temperature, this solution was diluted with ethyl acetate, the resulting insoluble matter was removed by Celite filtration, and washed with ethyl. The residue resulting from the removal of the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (328 mg) was obtained as a yellow oily substance.

Workup

  1. customthe resulting insoluble matter was removed by Celite filtration
  2. washwashed with ethyl
  3. customThe residue resulting from the removal of the solvent by evaporation
  4. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a9e73771af9944cfbe9115bc0c9c5c55
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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