(E)-methyl 2-(4-chlorophenyl)-2-(4-(2-(methylsulfonyl)vinyl)-1H-indol-1-yl)butanoate → Methyl 2-(4-chlorophenyl)-2-(4-(2-(methylsulfonyl)ethyl)-1H-indol-1-yl)butanoate

HRID 1477886Notes

Reaction equation

HRID 1477886 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19](/[CH:24]=[CH:25]/[S:26]([CH3:29])(=[O:28])=[O:27])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)([CH2:13][CH3:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([CH2:24][CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)([CH2:13][CH3:14])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86705049(E)-methyl 2-(4-chlorophenyl)-2-(4-(2-(methylsulfonyl)vinyl)-1H-indol-1-yl)butanoate

Product 1

HCID 70562004Methyl 2-(4-chlorophenyl)-2-(4-(2-(methylsulfonyl)ethyl)-1H-indol-1-yl)butanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-methyl 2-(4-chlorophenyl)-2-(4-(2-(methylsulfonyl)vinyl)-1H-indol-1-yl)butanoate (1.18 g, 2.73 mmol) in EtOAc (50 mL) was added Pd/C (10% on carbon, 0.2 g). The mixture was stirred under H2 atmosphere for 30 min. Then the reaction mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo. The residue was purified via column chromatography (0-30% EtOAc/hexanes) to provide the title compound. LC/MS m/z=434.1 [M+H]+.

Workup

  1. filtrationThen the reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified via column chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-70504ec2bd17451e983e30de59097b4a
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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