Potassium Carbonate → 3-(4-chlorophenoxy)-2-methyl-5-(methylthio)-1H-indole-1-acetic acid, methyl ester

HRID 2233748

Reaktionsgleichung

Reaktionsgleichung von HRID 2233748
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([S:16][CH3:17])[CH:14]=3)[NH:9][C:8]=2[CH3:18])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([S:16][CH3:17])[CH:14]=3)[N:9]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:8]=2[CH3:18])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 686171473-(4-chlorophenoxy)-2-methyl-5-(methylthio)-1H-indole

Produkt 1

HCID 866092333-(4-chlorophenoxy)-2-methyl-5-(methylthio)-1H-indole-1-acetic acid, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of the product from step (i) (0.45 g), potassium carbonate (0.415 g) and methyl bromoacetate (0.21 ml) in DMF (3 ml) was stirred at 50° C. for 3 h. The reaction was partitioned between ethylacetate/water. The organics were washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5-15% ethylacetate/iso-hexane. Yield 0.33 g

Aufarbeitung

  1. customThe reaction was partitioned between ethylacetate/water
  2. washThe organics were washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 5-15% ethylacetate/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-5bf74929cb0447b38305667a6ff681ba
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709521B2

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