Water → N-(3-fluorophenyl)-(1H-indazol-5-yl)sulfonamide

HRID 25369

Reaction equation

HRID 25369 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([S:18](Cl)(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH:11]=[N:10]1.C(OCC)(=O)C.O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][S:18]([C:14]2[CH:13]=[C:12]3[C:17](=[CH:16][CH:15]=2)[NH:9][N:10]=[CH:11]3)(=[O:20])=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 97423-FluoroanilineHCID 225671441H-Indazole-5-sulfonyl chloride

Product 1

HCID 10266270N-(3-fluorophenyl)-(1H-indazol-5-yl)sulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

N-(3-Fluorophenyl)-(1H-indazol-5-yl)sulfonamide can be obtained in the following way: 0.98 ml of 3-fluoroaniline is added dropwise to a solution, cooled to a temperature in the region of 0° C., of 2.57 g of (1H-indazol-5-yl)sulfonyl chloride in 40 ml of pyridine. Stirring is maintained for 2 hours at a temperature in the region of 0° C. and then for 18 hours at a temperature in the region of 20° C. The medium is concentrated by evaporation under reduced pressure, and the residue obtained is taken up with 50 ml of ethyl acetate and 40 ml of water. The organic phase is washed with 2 times 20 ml of water, dried over magnesium sulfate, filtered and concentrated by evaporation under reduced pressure. The residue obtained is purified by chromatography on a silica column with an ethyl acetate/cyclohexane (1/3 by volume) mixture as eluent. 8 mg of N-(3-fluorophenyl)-(1H-indazol-5-yl)sulfonamide are thus obtained in the form of an orange solid.

Workup

  1. concentrationThe medium is concentrated by evaporation under reduced pressure
  2. customthe residue obtained
  3. washThe organic phase is washed with 2 times 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue obtained
  8. customis purified by chromatography on a silica column with an ethyl acetate/cyclohexane (1/3 by volume) mixture as eluent

Sources & evidence

ORD record
ord-7aef0a420cdb497b899c709993003b79
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

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