HCID 19101761, Verbindung → HCID 19101763, Verbindung

HRID 1974567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1974567
[CH3:1][C:2]1[N:3]([C:17](=[O:27])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=2)[C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2>CO.O1CCOCC1.[Pd]>[NH2:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[C:17]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[C:2]1[CH3:1])=[O:27]

Komponenten

5

Edukt 1

HCID 19101761HCID 19101761, Verbindung

Produkt 1

HCID 19101763HCID 19101763, VerbindungAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 4-[2-methyl-1-(3-nitrobenzoyl)indol-3-yl]butyric acid (600 mg) in a mixture of methanol (30 ml) and 1,4-dioxane (30 ml) was added 10% palladium on activated carbon (300 mg), and the mixture was stirred under hydrogen atmosphere (3 atm) at 20° C. for 45 minutes. The catalyst was filtered off and the filtrate was evaporated. The residue was chromatographed on a silica gel column (25 ml) eluting with a mixture of chloroform and methanol (10:1) to give 4-[1-(3-aminobenzoyl)-2-methylindol-3-yl]butyric acid (490 mg) as a yellow foam.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on a silica gel column (25 ml)
  4. washeluting with a mixture of chloroform and methanol (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-a5307981bed04151a53dccfd6bad5d90
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05283251

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