Water → 1-acetyl-1H-indazol-5-yl 3-fluorobenzenesulfonate

HRID 25377노트

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HRID 25377 반응식
[F:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:12]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([OH:24])=[CH:21][CH:22]=2)[CH:17]=[N:16]1)(=[O:14])[CH3:13].C(N(CC)CC)C.O>O1CCCC1.C(OC(C)C)(C)C>[F:1][C:2]1[CH:3]=[C:4]([S:8]([O:24][C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[N:15]([C:12](=[O:14])[CH3:13])[N:16]=[CH:17]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 225670481-(5-hydroxy-1H-indazol-1-yl)-Ethanone

생성물 1

HCID 225671041-acetyl-1H-indazol-5-yl 3-fluorobenzenesulfonate

시약·촉매·용매 2

HCID 7914Diisopropyl Ether용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

1-Acetyl-1H-indazol-5-yl 3-fluorobenzenesulfonate can be obtained in the following way: a solution de 0.15 g of 3-fluorobenzenesulfonyl chloride in 2 ml of tetrahydrofuran is run in dropwise into a solution, cooled to a temperature in the region of 0° C., of 132 mg of 1-acetyl-5-hydroxy-1H-indazole in 5 ml of anhydrous tetrahydrofuran and of 0.2 ml of triethylamine. The reaction medium is maintained with stirring for 3 hours at a temperature in the region of 0° C. and is then brought back to a temperature in the region of 20° C., hydrolyzed with 15 ml of distilled water and extracted with three times 15 ml of ethyl acetate. The pooled organic extracts are dried over magnesium sulfate, filtered and concentrated under reduced pressure. A white powder is thus obtained, which powder is resuspended in diisopropyl ether, separated by filtration, washed with diisopropyl ether and dried under reduced pressure. 193 mg of 1-acetyl-1H-indazol-5-yl 3-fluorobenzenesulfonate are thus obtained in the form of a white solid (Rf=0.50, silica gel thin layer chromatography, eluent: cyclohexane/dichloromethane (1/9 by volume)).

후처리

  1. temperatureThe reaction medium is maintained
  2. extractionextracted with three times 15 ml of ethyl acetate
  3. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customA white powder is thus obtained
  7. customseparated by filtration
  8. washwashed with diisopropyl ether
  9. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-0543ca052d314e10967b835187218824
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858638B2

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