3-(1H-Indol-6-yl)-3-(1H-indol-3-yl)-acrylic acid ethyl ester → 3-(1H-Indol-6-yl)-3-(1H-indol-3-yl)-propionic acid ethyl ester

HRID 1716637Notes

Reaction equation

HRID 1716637 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[C:6]([C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[CH:21][NH:22]2)=[CH:18][CH:17]=1)[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[CH3:2]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]([C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[CH:21][NH:22]2)=[CH:18][CH:17]=1)[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 673553193-(1H-Indol-6-yl)-3-(1H-indol-3-yl)-acrylic acid ethyl ester

Product 1

HCID 598316643-(1H-Indol-6-yl)-3-(1H-indol-3-yl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(1H-indol-6-yl)-3-(1H-indol-3-yl)-acrylic acid ethyl ester XXVI in ethanol (15 ml) was added catalytic quantity of Pd(OH)2/C (20%). The reaction mixture was hydrogenated in a Parr apparatus under 55 psi of H2 for 24 hours. The catalyst was removed by filtration through a pad of celite with MeOH. The filtrate was concentrated to afford 3-(1H-indol-6-yl)-3-(1H-indol-3-yl)-propionic acid ethyl ester XXVII (241 mg) as a light brown solid, which was used in the next reaction without purification.

Workup

  1. customThe catalyst was removed by filtration through a pad of celite with MeOH
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5f8ef45aa73d40e8a352edcbb47913d3
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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