Cesium carbonate → 5-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester

HRID 49047

Reaktionsgleichung

Reaktionsgleichung von HRID 49047
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

Produkt 1

HCID 695874395-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl esterAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (2 g, 10 mmol), tert-butyl bromoacetate (2.35 g, 12 mmol) and cesium carbonate (10.5 g, 30 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate (150 mL), washed with water (5×50 mL) and brine, dried and concentrated. The residue was recrystallized from ethyl acetate and hexane to give 2 g (63%) 5-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester.

Aufarbeitung

  1. washwashed with water (5×50 mL) and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was recrystallized from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-2164c929345b4daca0809a4439a86791
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706709B2

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