5-Chlorooxindole → 4-(2-ethoxycarbonylethyl)-3-methyl-5-(5-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 24535

Reaktionsgleichung

Reaktionsgleichung von HRID 24535
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH:19]=O)=[C:9]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]=1[CH3:11])=[O:5])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26](=[O:31])[CH2:25]2>N1CCCCC1.C(O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH:19]=[C:25]2[C:24]3[C:28](=[CH:29][CH:30]=[C:22]([Cl:21])[CH:23]=3)[NH:27][C:26]2=[O:31])=[C:9]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 1528015-ChlorooxindoleHCID 110223335-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Produkt 1

HCID 539693984-(2-ethoxycarbonylethyl)-3-methyl-5-(5-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid ethyl esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

5-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (281 mg), 5-chloro-2-oxindole (168 mg), and piperidine (2 drops) in ethanol (2 mL) were refluxed for 2 hours. The reaction mixture was cooled and the precipitate that formed was filtered, washed with ethanol and hexanes, and dried to give 369 mg (86%) of 4-(2-ethoxycarbonylethyl)-3-methyl-5-(5-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid ethyl ester as a light yellow needle crystals.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customthe precipitate that formed
  3. filtrationwas filtered
  4. washwashed with ethanol and hexanes
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e1888cbc890c4753983419f82796c0fa
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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