Sodium Hydroxide → 4-((6-(2-Ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-amine

HRID 1427040

반응식

HRID 1427040 반응식
[OH-].[Na+].[CH2:3]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:25]C(=O)C)[CH:20]=1)[CH3:4]>CO.C(OCC)(=O)C.O>[CH2:3]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=1)[CH3:4]

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 86730342N-(4-((6-(2-Ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide

생성물 1

HCID 867303434-((6-(2-Ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-amine수율 87%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
75 °C

실험 절차

A 2 M sodium hydroxide solution (20 mL) was added to a solution of N-(4-((6-(2-ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide described in Production Example 24-6 (2.5 g, 7.04 mmol) in methanol (20 mL) under nitrogen atmosphere at room temperature, and the mixture was heated and stirred under reflux at 75° C. for 2 hours. The reaction liquid was allowed to stand to cool to room temperature and then diluted with ethyl acetate and water. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=1:9-0:1-ethyl acetate:methanol=49:1-24:1) to obtain the title compound (1.92 g, 87%).

후처리

  1. temperaturethe mixture was heated
  2. customThe reaction liquid
  3. temperatureto cool to room temperature
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe filtrate was concentrated under vacuum
  8. customThe resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=1:9-0:1-ethyl acetate:methanol=49:1-24:1)

출처 및 근거

ORD 기록
ord-43f451f4af754f318978d73a2566045f
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933099B2

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