2-Fluoro-5-(trifluoromethyl)benzene-1-sulfonyl chloride → 3-[4-(2-Fluoro-5-trifluoromethylbenzenesulfonylamino)phenyl]-1H-indole-2-carboxamide

HRID 230552Notes

Reaction equation

HRID 230552 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12](Cl)(=[O:14])=[O:13].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][C:24]=2[C:32]([NH2:34])=[O:33])=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH:25][C:24]=2[C:32]([NH2:34])=[O:33])=[CH:21][CH:22]=1)(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 27375472-Fluoro-5-(trifluoromethyl)benzene-1-sulfonyl chlorideHCID 577628333-(4-Aminophenyl)-1H-indole-2-carboxamide

Product 1

HCID 116198893-[4-(2-Fluoro-5-trifluoromethylbenzenesulfonylamino)phenyl]-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

162 mg of 2-fluoro-5-trifluoromethylphenylsulfonyl chloride in 6 ml of pyridine are added dropwise to a solution of 100 mg of 3-(4-aminophenyl)-1H-indole-2-carboxamide (example 1) in 12 ml of pyridine at 0° C. The mixture is stirred at ambient temperature for 6 hours and then poured into 50 ml of ice-cold water, and the precipitate formed is filtered off. After purification by flash chromatography on a silica column, elution being carried out with a mixture of cyclohexane and ethyl acetate (20/80 by volume), 50 mg of 3-[4-(2-fluoro-5-trifluoromethylbenzenesulfonylamino)phenyl]-1H-indole-2-carboxamide are obtained, the characteristics of which are as follows:

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. customAfter purification by flash chromatography
  4. washon a silica column, elution
  5. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (20/80 by volume), 50 mg of 3-[4-(2-fluoro-5-trifluoromethylbenzenesulfonylamino)phenyl]-1H-indole-2-carboxamide
  6. customare obtained

Sources & evidence

ORD record
ord-b45ca98aeefc46188696ded7fd98f9b5
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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