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

HRID 1790893

Reaktionsgleichung

Reaktionsgleichung von HRID 1790893
[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].Cl[CH2:17][C:18]([N:20]([CH3:22])[CH3:21])=[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:19])[N:20]([CH3:22])[CH3:21])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

Produkt 1

HCID 695870655-dimethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl esterAusbeute 48,2 %

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), 2-chloro-N,N-dimethylacetamide (1.33 g, 11 mmol) and cesium carbonate (9.8 g, 30 mmol)) in dimethylformamide (20 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 1.4 g of 5-dimethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl ester as a brown solid.

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-08e9eb19e15d4e6fa1eb511e4a67f7f7
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071332B2

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