Ethyl bromoacetate → 3-(4-Chlorophenoxy)-5-fluoro-2-methyl-1H-indole-1-acetic acid, ethyl ester

HRID 2233736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233736
[H-].[Na+].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=3)[NH:11][C:10]=2[CH3:19])=[CH:6][CH:5]=1.[CH2:22]([O:24][C:25](=[O:28])[CH2:26]Br)[CH3:23]>CN(C=O)C>[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=3)[N:11]([CH2:26][C:25]([O:24][CH2:22][CH3:23])=[O:28])[C:10]=2[CH3:19])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 117018033-(4-chlorophenoxy)-5-fluoro-2-methyl-1H-indole

Produkt 1

HCID 116391123-(4-Chlorophenoxy)-5-fluoro-2-methyl-1H-indole-1-acetic acid, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% disp. in oil) (0.12 g) was added portionwise to a stirred solution of the product from step (i) (0.75 g) in DMF (10 ml) at RT. After 10 min, ethylbromoacetate (345 ul) was added, the mixture stirred at RT for 3 h then quenched with water and extracted with diethylether. The organics were washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 15% ethylacetate/iso-hexane. Yield 0.38 g

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-98599851cedc4c0681ce216a1ddf37e1
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709521B2

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