2-[[(E)-2-(4-Benzofuran-2-ylphenyl)ethenyl]sulfonylamino]benzenesulfonamide → 2-[2-(4-Benzofuran-2-ylphenyl)ethylsulfonylamino]benzenesulfonamide

HRID 2283258Notes

Reaction equation

HRID 2283258 reaction equation
[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:16]=[CH:17]/[S:18]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([NH2:31])(=[O:30])=[O:29])(=[O:20])=[O:19].[H][H]>C(OCC)(=O)C.[Pd]>[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][S:18]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([NH2:31])(=[O:30])=[O:29])(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 866319992-[[(E)-2-(4-Benzofuran-2-ylphenyl)ethenyl]sulfonylamino]benzenesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 687852732-[2-(4-Benzofuran-2-ylphenyl)ethylsulfonylamino]benzenesulfonamideYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-[[(E)-2-(4-Benzofuran-2-ylphenyl)ethenyl]sulfonylamino]benzenesulfonamide (Example 3, 43 mg, 95 μmol) was dissolved in ethyl acetate (5 ml) and subjected to the H-cube (1 ml/min, full hydrogen. 10% Pd/C). The material obtained was purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound (12 mg, 28%) as a white solid. The compound of Example 2 was also obtained.

Workup

  1. customThe material obtained
  2. customwas purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer)

Sources & evidence

ORD record
ord-9216dfc5c0b14344a5c91d85d8844b31
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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