Benzenesulfonyl chloride → HCID 22025326, compound

HRID 1792837Notes

Reaction equation

HRID 1792837 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([CH3:13])[CH:3]=1.[H-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.CCOC(C)=O>[C:16]1([S:22]([N:8]2[C:9]3[C:5](=[C:4]([CH3:13])[CH:3]=[C:2]([Cl:1])[C:10]=3[O:11][CH3:12])[CH:6]=[N:7]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 22025340HCID 22025340, compound

Product 1

HCID 22025326HCID 22025326, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

6-Chloro-7-methoxy-4-methyl-1H-indazole (1.55 g, 9.2 mmol) is dissolved in THF (50 mL) and cooled to 0° C. Sodium hydride (60% in mineral oil, 0.40 g, 10 mmol) is added and the reaction is stirred 10 min. Benzenesulfonyl chloride (1.2 mL, 9.7 mmol) is added and the reaction is stirred 20 min. The reaction is diluted with EtOAc, washed with a solution of NH4Cl, water, brine and dried with MgSO4. The solution is concentrated and triturated with hexane to provide 1-benzenesulfonyl-6-chloro-7-methoxy-4-methyl-1H-indazole which is used without further purification.

Workup

  1. stirringthe reaction is stirred 20 min
  2. washwashed with a solution of NH4Cl, water, brine
  3. dry with materialdried with MgSO4
  4. concentrationThe solution is concentrated
  5. customtriturated with hexane

Sources & evidence

ORD record
ord-c5e831d81db04554ad370dbf099ba58f
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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