Water → N-(4-((6-(2-Methoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide

HRID 1427031

Reaktionsgleichung

Reaktionsgleichung von HRID 1427031
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][C:7]=1[OH:15].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=1.CC(C)([O-])C.[K+].O>CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][C:7]=1[O:15][C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 22832129N-(4-Chloropyridin-2-yl)acetamideHCID 23665647Potassium tert-butoxideHCID 867303346-(2-Methoxyethoxy)-1H-indol-5-ol

Produkt 1

HCID 86730333N-(4-((6-(2-Methoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

6-(2-Methoxyethoxy)-1H-indol-5-ol described in Production Example 20-4 (3.94 g, 19.0 mmol) and N-(4-chloropyridin-2-yl)acetamide described in Production Example 1-5 (3.25 g, 19.0 mmol) were dissolved in dimethylsulfoxide (25 mL), then 97% potassium tert-butoxide (2.20 g, 19.0 mmol) was added at room temperature, and the mixture was heated and stirred at 150° C. for 13 hours. Water and ethyl acetate were added to the reaction liquid at mom temperature for partition. The aqueous layer was extracted with ethyl acetate three times and the combined organic layer was washed with water. The organic layer was dried over anhydrous sodium sulfate. The drying agent was filtered off and the filtrate was concentrated under vacuum, and then the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=2:3-0:1-ethyl acetate:methanol=49:1-9:1). The target fraction was concentrated under vacuum to obtain the title compound (3.45 g, 53%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. customfor partition
  3. extractionThe aqueous layer was extracted with ethyl acetate three times
  4. washthe combined organic layer was washed with water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under vacuum
  8. customthe resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=2:3-0:1-ethyl acetate:methanol=49:1-9:1)
  9. concentrationThe target fraction was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-25142853aac24ca7aca447f92bb9bbba
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933099B2

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