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

HRID 1860935

Reaktionsgleichung

Reaktionsgleichung von HRID 1860935
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH:18]=O)=[C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:10]=1[CH3:11])=[O:5])[CH3:2].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29]>N1CCCCC1.C(O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH:18]=[C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:20][C:21]2=[O:29])=[C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 321710OxindoleHCID 155335575-(Ethoxycarbonyl)-2-formyl-4-methyl-1H-pyrrole-3-propanoic Acid Methyl Ester

Produkt 1

HCID 537772934-(2-Methoxycarbonyl-ethyl)-3-methyl-5-(2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid ethyl esterAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

5-Formyl-4-(2-methoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (80.2 g), 2-oxindole (37.9 g) and ethanol (300 mL) were warmed to 70° C. in a 500 mL, 3-neck round bottom flask equipped with mechanical stirring and a reflux condenser. Piperidine (1.3 g) was added and the mixture was refluxed for 4 hours. The mixture was cooled to 10° C. and the orange precipitate collected by vacuum filtration and washed with 30 mL of ethanol. The solid was slurry-washed in 150 mL of refluxing ethanol, cooled, collected by vacuum filtration, washed with 30 mL of ethanol and vacuum dried to give 81.7 g (75%) of 4-(2-Methoxycarbonylethyl)-3-methyl-5-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid ethyl ester as an orange solid.

Aufarbeitung

  1. customequipped
  2. temperaturethe mixture was refluxed for 4 hours
  3. filtrationthe orange precipitate collected by vacuum filtration
  4. washwashed with 30 mL of ethanol
  5. washThe solid was slurry-washed in 150 mL of refluxing ethanol
  6. temperaturecooled
  7. filtrationcollected by vacuum filtration
  8. washwashed with 30 mL of ethanol and vacuum
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9d84529eeb5e4d67a74832536e51017c
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531502B1

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