3-(Trifluoromethyl)benzenesulfonyl chloride → HCID 46234072, compound

HRID 407163Notes

Reaction equation

HRID 407163 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:13][NH:14]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[F:22][C:23]([F:35])([F:34])[C:24]1[CH:25]=[C:26]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1>N1C=CC=CC=1>[F:35][C:23]([F:22])([F:34])[C:24]1[CH:25]=[C:26]([S:30]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[CH:16]=[C:15]4[C:11]([C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:13][NH:14]4)=[CH:10][CH:9]=3)[CH:5]=[CH:6][CH:7]=2)(=[O:31])=[O:32])[CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 46235778HCID 46235778, compound

Product 1

HCID 46234072HCID 46234072, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of ethyl 6-(3-aminophenyl)-1H-indazole-3-carboxylate (10 mg) in pyridine (1 Ml), was added 3-trifluoromethylbenzenesulfonyl chloride (6.3 μl) at room temperature. After 3 h, pyridine was removed by evaporation. Ethyl acetate and water were added and the aqueous layer was extracted with ethyl acetate three times. The combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was triturated in ethyl acetate/hexane to give ethyl 6-(3-(3-(trifluoromethyl)phenylsulfonamido)phenyl)-1H-indazole-3-carboxylate (8.6 mg).

Workup

  1. custompyridine was removed by evaporation
  2. additionEthyl acetate and water were added
  3. extractionthe aqueous layer was extracted with ethyl acetate three times
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated in ethyl acetate/hexane

Sources & evidence

ORD record
ord-438d64a14e1744adb0f0592139139c9a
Source dataset
uspto-grants-2014_06
Patent number
US08754209B2

Reaction notes

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