5-fluoro-1,3-dihydro-2H-indol-2-one → 5-(5-Fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

HRID 349864

Reaktionsgleichung

Reaktionsgleichung von HRID 349864
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH:12]([C:14]1[NH:18][C:17]([CH3:19])=[C:16]([C:20]([OH:22])=[O:21])[C:15]=1[CH3:23])=O>N1CCCCC1.C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:14]1[NH:18][C:17]([CH3:19])=[C:16]([C:20]([OH:22])=[O:21])[C:15]=1[CH3:23]

Komponenten

5

Edukt 2

HCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 110737925-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid

Produkt 1

HCID 533951025-(5-Fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acidAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The reaction mixture of 5-fluorooxindole (100 mg, 0.66 mmol), 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (133 mg, 0.79 mmol), and 10 drops of piperidine in ethanol (3 mL) was stirred at 60° C. overnight and filtered. The solid was washed with 1 M of aqueous hydrochloride solution, water, and dried to afford 5-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (201 mg, quantitative) as a yellow solid. MS m/z (relative intensity, %) 299 ([M−1]+., 100).

Aufarbeitung

  1. filtrationfiltered
  2. washThe solid was washed with 1 M of aqueous hydrochloride solution, water
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5a1ac89513dd4fe09cb21b3a8bc68c56
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179910B2

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