3-(3-Cyano-1H-Indol-5-yl)-3-phenyl-acrylic acid ethyl ester → 3-(3-Cyano-1H-Indol-5-yl)-3-phenyl-propionic acid ethyl ester

HRID 1716670Notes

Reaction equation

HRID 1716670 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[C:6]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[C:22]#[N:23])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>CCO.CCOC(C)=O.CO.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[C:22]#[N:23])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 673561313-(3-Cyano-1H-Indol-5-yl)-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 673558733-(3-Cyano-1H-Indol-5-yl)-3-phenyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18423184Ethyl acetate ethanol methanolSolvent

Procedure

To a solution of 3-(3-cyano-1H-Indol-5-yl)-3-phenyl-acrylic acid ethyl ester LXIII (1.81 g, 5.71 mmol) in EtOH/EtOAc/MeOH (1/1/1, 60 ml) was added a catalytic amount of Pd/C (5%). The mixture was hydrogenated in a Parr apparatus at 60 psi of H2 for 19 hours, filtered through celite, and the filter cake was washed with MeOH and EtOAc. The filtrate was concentrated to afford 3-(3-Cyano-1H-Indol-5-yl)-3-phenyl-propionic acid ethyl ester LXIV as a white foamy solid in quantitative yield (1.86 g).

Workup

  1. filtrationfiltered through celite
  2. washthe filter cake was washed with MeOH and EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-787bd03ef3db4b19bed37d28e12c400e
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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