Ethyl Acetate → 3-(3-cyano-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

HRID 1716665Notes

Reaction equation

HRID 1716665 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[C:6]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:22]#[N:23])=[CH:16][NH:17]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].CCOC(C)=O>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:22]#[N:23])=[CH:16][NH:17]2)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 673553223-(3-cyano-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 673560383-(3-cyano-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(3-cyano-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester LVIII (620 mg, 1.96 mmol) in EtOH (30 ml) and EtOAc (15 ml) was added Degoussa-type catalyst (10% Pd/C wet, 70 mg). The reaction mixture was hydrogenated in a Parr apparatus at 55 psi of H2 for 19 hours. The reaction mixture was filtered through celite with EtOH, MeOH and EtOAc. The filtrate was concentrated to afford 3-(3-cyano-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester LIX as a white solid in quantitative yield (648 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite with EtOH, MeOH and EtOAc
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d083fd49360e4ee09db2e855e1dca8c1
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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