Sodium Thiosulfate → 3-chloro-2-(2-ethylsulfonylphenyl)-6-trifluoromethyl-2H-indazole

HRID 918779Notes

Reaction equation

HRID 918779 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:20]=[C:19]2[C:14]([CH:15]=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:18]2)=[N:13]1)(=[O:5])=[O:4])[CH3:2].[Cl:25]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[Cl:25][C:20]1[N:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[N:13]=[C:14]2[C:19]=1[CH:18]=[CH:17][C:16]([C:21]([F:23])([F:24])[F:22])=[CH:15]2

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 727036622-(2-ethylsulfonylphenyl)-6-trifluoromethyl-2H-indazole

Product 1

HCID 727038603-chloro-2-(2-ethylsulfonylphenyl)-6-trifluoromethyl-2H-indazoleYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 226 mg of 2-(2-ethylsulfonylphenyl)-6-trifluoromethyl-2H-indazole, 86 mg of N-chlorosuccinimide and 2 ml of DMF was stirred at room temperature for 10 hours. A 10% aqueous sodium thiosulfate solution was poured to the reaction mixture, and the mixture was extracted with t-butyl methyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The resulting residue was washed with n-hexane to obtain 250 mg of 3-chloro-2-(2-ethylsulfonylphenyl)-6-trifluoromethyl-2H-indazole (hereinafter, referred to as Compound of Present Invention 3).

Workup

  1. extractionthe mixture was extracted with t-butyl methyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting residue was washed with n-hexane

Sources & evidence

ORD record
ord-3888f7a4df22403fadecfbef95e3f411
Source dataset
uspto-grants-2016_03
Patent number
US09271500B2

Reaction notes

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