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 1716670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716670
[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]

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 18423184Ethyl acetate ethanol methanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-787bd03ef3db4b19bed37d28e12c400e
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803830B2

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