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

HRID 25377ノート

反応式

HRID 25377 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 7914Diisopropyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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)).

後処理

  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

出典と根拠

ORDレコード
ord-0543ca052d314e10967b835187218824
出典データセット
uspto-grants-2005_02
特許番号
US06858638B2

反応ノート

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