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

HRID 1427032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427032
[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:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH:22]C(=O)C)[CH:17]=1.[OH-].[Na+].O.C(OCC)(=O)C>CO>[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:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[CH:17]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86730333N-(4-((6-(2-Methoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide

Produkt 1

HCID 867303354-((6-(2-Methoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-amineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

N-(4-((6-(2-methoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide described in Production Example 20-5 (3.45 g, 10.1 mmol) was dissolved in methanol (50 mL), a 2 M sodium hydroxide solution (50 mL) was added at room temperature, and the mixture was heated and stirred at 70° C. for 3 hours. Water and ethyl acetate were added to the reaction mixture for partition. The aqueous layer was extracted with ethyl acetate three times and the combined organic layer was dried over anhydrous sodium sulfate. The drying agent was filtered off and the filtrate was concentrated under vacuum and the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=3:7-0:1-ethyl acetate:methanol=49:1-24:1). The target fraction and the mixture fraction were concentrated under vacuum separately from each other, the mixture fraction was purified again with silica gel column chromatography (ethyl acetate:methanol=1:0-9:1), and then the resultant was combined with the above-described target fraction to obtain the title compound (2.60 g, 86%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. customfor partition
  3. extractionThe aqueous layer was extracted with ethyl acetate three times
  4. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated under vacuum
  7. customthe resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=3:7-0:1-ethyl acetate:methanol=49:1-24:1)
  8. concentrationThe target fraction and the mixture fraction were concentrated under vacuum separately from each other, the mixture fraction
  9. customwas purified again with silica gel column chromatography (ethyl acetate:methanol=1:0-9:1)

Quellen und Nachweise

ORD-Eintrag
ord-65ab05951d2e4e1d92f3310de9a714cc
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933099B2

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