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

HRID 1427020

반응식

HRID 1427020 반응식
[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[OH:14])([CH3:3])[CH3:2].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23](=[O:25])[CH3:24])[CH:17]=1.CC(C)([O-])C.[K+].O>CS(C)=O.C(OCC)(=O)C>[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:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23](=[O:25])[CH3:24])[CH:17]=1)([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 22832129N-(4-Chloropyridin-2-yl)acetamideHCID 23665647Potassium tert-butoxideHCID 867303236-Isopropoxy-1H-indol-5-ol

생성물 1

HCID 86730322N-(4-((6-Isopropoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide수율 41%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
160 °C

실험 절차

6-Isopropoxy-1H-indol-5-ol described in Production Example 17-4 (165 mg, 0.863 mmol) and N-(4-chloropyridin-2-yl)acetamide described in Production Example 1-5 (442 mg, 2.59 mmol) were dissolved in dimethylsulfoxide (2.0 mL) under nitrogen atmosphere, then potassium tert-butoxide (194 mg, 1.73 mmol) was added at room temperature, and the mixture was heated and stirred at 160° C. for 3 hours. The reaction liquid was cooled to room temperature and water and ethyl acetate were added for partition. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with water and a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate and then filtered, then the filtrate was concentrated under vacuum. The residue was dissolved in dichloromethane, the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=3:2-1:3), and then the target fraction was concentrated under vacuum to obtain the title compound (116 mg, 41%).

후처리

  1. temperaturethe mixture was heated
  2. customThe reaction liquid
  3. temperaturewas cooled to room temperature
  4. customfor partition
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe combined organic layer was washed with water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under vacuum
  10. dissolutionThe residue was dissolved in dichloromethane
  11. customthe resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=3:2-1:3)
  12. concentrationthe target fraction was concentrated under vacuum

출처 및 근거

ORD 기록
ord-b389ce7c2d0747fb96efdf847a7a487f
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933099B2

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