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

HRID 1452845Notes

Reaction equation

HRID 1452845 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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)).

Workup

  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

Sources & evidence

ORD record
ord-d5f3dcb6c2d04cdcb3ab343461d94224
Source dataset
uspto-grants-2009_01
Patent number
US07473701B2

Reaction notes

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