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

HRID 1427031

반응식

HRID 1427031 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
150 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-25142853aac24ca7aca447f92bb9bbba
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933099B2

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