5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide → HCID 24804767, Verbindung
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18]CC3C=CC=CC=3)[CH:16]=2)[N:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]=1[CH3:32])=[O:8]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[F:36])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[N:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]=1[CH3:32])=[O:8]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a mixture of 5-benzyloxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluoro-benzylamide (Compound 56, 0.15 g, 0.31 mmol) in methanol (15 ml), which was degassed with argon for 10 min, was added 10% palladium on carbon (0.17 g), with continued degassing. The reaction was placed in par tube on hydrogenator and hydrogenated at 45 psi for 18 h. The reaction was then filtered, concentrated under reduced pressure and the crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes) to yield 5-hydroxy-2-methyl-1-phenyl-1H-indole-3-carboxylic acid, 3,4-difluorobenzylamide (Compound 29) as a solid (0.11 g, 92%).
Aufarbeitung
- customwas degassed with argon for 10 min
- additionwas added 10% palladium on carbon (0.17 g)
- filtrationThe reaction was then filtered
- concentrationconcentrated under reduced pressure
- customthe crude product residue was purified by flash column chromatography on silica gel (30% EtOAc-hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-b67d2a2af3e84a65b22ba81bd6e15ab7
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07737173B2
Notizen zur Reaktion
Wird geladen…