5-{4-[2-(Indol-1-yl)ethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione → 5-((4-(2-(1H-Indol-1-yl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione

HRID 1601765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1601765
[N:1]1([CH2:10][CH2:11][O:12][C:13]2[CH:45]=[CH:44][C:16]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[N:20](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:19]3=[O:43])=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H][H]>O1CCOCC1.[Pd]>[N:1]1([CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:43])=[CH:44][CH:45]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

5

Edukt 2

HCID 232983005-{4-[2-(Indol-1-yl)ethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dioneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 1540055-((4-(2-(1H-Indol-1-yl)ethoxy)phenyl)methyl)-2,4-thiazolidinedioneAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2.05 g of 5-{4-[2-(indol-1-yl)-ethoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 14) in 100 ml of dioxane was stirred in an atmosphere of hydrogen and in the presence of 3.1 g of 10% w/w palladium-on-charcoal, first at room temperature for 30 minutes, then at 60° C. for 2 hours and then at 80° C. for 3 hours. At the end of this time, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was then purified by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.06 g of the title compound, melting at 42.3-44.6° C.

Aufarbeitung

  1. waitat 80° C. for 3 hours
  2. filtrationAt the end of this time, the reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  5. customThe concentrate was then purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-5440b92b62ac47abb73bad562c6d2a83
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977365

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