Diisopropylethylamine → Ethyl(6-((2,4-dichlorobenzyl)sulfanyl)-1-benzothiophen-3-yl)acetate

HRID 591487Notes

Reaction equation

HRID 591487 reaction equation
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CCN(C(C)C)C(C)C.[Cl:52][C:53]1[CH:60]=[C:59]([Cl:61])[CH:58]=[CH:57][C:54]=1[CH2:55][SH:56].[CH2:62]([O:64][C:65](=[O:84])[CH2:66][C:67]1[C:71]2[CH:72]=[CH:73][C:74](OS(C(F)(F)F)(=O)=O)=[CH:75][C:70]=2[S:69][CH:68]=1)[CH3:63]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:62]([O:64][C:65](=[O:84])[CH2:66][C:67]1[C:71]2[CH:72]=[CH:73][C:74]([S:56][CH2:55][C:54]3[CH:57]=[CH:58][C:59]([Cl:61])=[CH:60][C:53]=3[Cl:52])=[CH:75][C:70]=2[S:69][CH:68]=1)[CH3:63]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 957562,4-DichlorobenzenemethanethiolHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57443344Ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 118667019Ethyl(6-((2,4-dichlorobenzyl)sulfanyl)-1-benzothiophen-3-yl)acetate

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (15.71 mg), DIPEA (0.187 ml), 2,4-dichlorobenzyl mercaptan (0.085 mL) and ethyl(6-(((trifluoromethyl)sulfonyl)oxy)-1-benzothiophen-3-yl)acetate (200 mg) in toluene (6 mL) was added tris(dibenzylideneacetone)dipalladium(0) (24.86 mg) at room temperature. The mixture was refluxed 1.5 h. After cooling, water was poured into mixture, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (238 mg).

Workup

  1. temperatureThe mixture was refluxed 1.5 h
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-4361cea35fb54252a4bfb996d57628d2
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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