Methyl iodide → ethyl 7-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate

HRID 1880362노트

반응식

HRID 1880362 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[C:6]2[C:10]=1[N:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:8]=[CH:7]2.[C:22]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH3:22][O:1][C:2]1[CH:3]=[C:4]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[C:6]2[C:10]=1[N:9]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:8]=[CH:7]2

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66920492Ethyl 7-hydroxy-1-tetrahydropyran-2-YL-indazole-5-carboxylate

생성물 1

HCID 66920406ethyl 7-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate수율 92%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of ethyl 7-hydroxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate (1.45 g, 5.0 mmol) in acetone (20 mL) containing K2CO3 (760 mg, 5.50 mmol) was added iodomethane (781 mg, 0.34 mL, 5.5 mmo). The mixture was heated at reflux under N2 overnight. The mixture was cooled to room temperature, filtered, evaporated and partitioned between EtOAc and water. The aqueous phase was extracted with additional EtOAc. The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated to provide crude product. The crude material was purified by chromatography (Isco, 0-40% EtOAc/heptane) to provide material which was dried under high vacuum overnight to afford ethyl 7-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate (1.40 g, 92%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux under N2 overnight
  3. filtrationfiltered
  4. customevaporated
  5. custompartitioned between EtOAc and water
  6. extractionThe aqueous phase was extracted with additional EtOAc
  7. washThe combined organic extracts were washed with saturated aqueous NaCl
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto provide crude product
  12. customThe crude material was purified by chromatography (Isco, 0-40% EtOAc/heptane)
  13. customto provide material which
  14. customwas dried under high vacuum overnight

출처 및 근거

ORD 기록
ord-be8145f0082545c3a098be7ec0e1471c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318762B2

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