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

HRID 1427021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427021
[CH:1]([O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][C:6]=1[O:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH:21]C(=O)C)[CH:16]=1)([CH3:3])[CH3:2].C[O-].[Na+].O.C(OCC)(=O)C>CO>[CH:1]([O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][C:6]=1[O:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=1)([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 86730322N-(4-((6-Isopropoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide

Produkt 1

HCID 867303244-((6-Isopropoxy-1H-indol-5-yl)oxy)pyridin-2-amineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

N-(4-((6-isopropoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide described in Production Example 17-5 (116 mg, 0.357 mmol) was dissolved in methanol (2.5 mL), 28% sodium methoxide (0.728 mL) was added under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature and then water and ethyl acetate were added for partition. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was filtered off and the resultant was concentrated under vacuum. The residue was dissolved in dichloromethane and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=3:7-0:1-ethyl acetate:methanol=99:1-9:1), then the target fraction was concentrated under vacuum to obtain the title compound (66.3 mg, 66%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customfor partition
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe resultant was concentrated under vacuum
  8. dissolutionThe residue was dissolved in dichloromethane
  9. customthe resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=3:7-0:1-ethyl acetate:methanol=99:1-9:1)
  10. concentrationthe target fraction was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7351a794a4af424abfa4222e96c151a8
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933099B2

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