6-(3-Ethoxyphenyl)indolin-2-one → 3-{5-[6-(3-Ethoxy-phenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid

HRID 1243477

Reaktionsgleichung

Reaktionsgleichung von HRID 1243477
[C:1]([CH2:4][CH2:5][C:6]1[C:7]([CH3:13])=[C:8]([CH:11]=O)[NH:9][CH:10]=1)([OH:3])=[O:2].[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:31]=[C:30]3[C:26]([CH2:27][C:28](=[O:32])[NH:29]3)=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1)[CH3:15]>N1CCCCC1.C(O)C>[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:31]=[C:30]3[C:26]([C:27](=[CH:11][C:8]4[NH:9][CH:10]=[C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:7]=4[CH3:13])[C:28](=[O:32])[NH:29]3)=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1)[CH3:15]

Komponenten

5

Edukt 2

HCID 106346366-(3-Ethoxyphenyl)indolin-2-oneHCID 151607523-(5-formyl-4-methyl-1H-pyrrol-3-yl)propanoic acid

Produkt 1

HCID 540922703-{5-[6-(3-Ethoxy-phenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acidAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

4-(2-carboxyethyl)-2-formyl-3-methylpyrrole (90.5 mg), 127 mg 6-(3-ethoxyphenyl)-2-oxindole and 2 drops piperidine in 2 mL of ethanol were heated at 90° C. overnight. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 200 mg (96%) of the title compound as a brown solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe precipitate was filtered
  4. washwashed with water to pH 6
  5. customdried in a vacuum oven overnight

Quellen und Nachweise

ORD-Eintrag
ord-c7763fa40b8a4b84a83f3b6a1bcfe6b4
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119090B2

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