p-Bromobenzenesulfonyl chloride → HCID 57992298, compound

HRID 1921240Notes

Reaction equation

HRID 1921240 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[ClH:12].[F:13][C:14]([F:31])([F:30])[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][CH2:25][CH2:24]3)=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:26]2[C:27]3[C:23](=[CH:22][C:21]([C:18]4[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:30])[F:31])=[CH:20][CH:19]=4)=[CH:29][CH:28]=3)[CH2:24][CH2:25]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[Cl:12]

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 67492862HCID 67492862, compound

Product 1

HCID 57992298HCID 57992298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.79 g of commercially available 4-bromo-benzenesulfonyl chloride were dissolved in 35 ml dichloromethane. Then 1.85 g 5-(4-trifluoromethyl-phenyl)-2,3-dihydro-1H-indole hydrochloride were added followed by 2.14 ml triethylamine. The mixture was stirred at room temperature for fifteen minutes. Then 100 ml of dichloromethane were added, the mixture washed with 40 ml water and brine and then dried over MgSO4. The solvent was removed in vacuo to obtain 2.48 g crude 1-(4-bromo-3-chloro-benzenesulfonyl)-5-(4-trifluoromethyl-phenyl)-2,3-dihydro-1H-indole. This material was used without further purification.

Workup

  1. washthe mixture washed with 40 ml water and brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-be93c85e8002490bbee008444058ae3a
Source dataset
uspto-grants-2012_05
Patent number
US08173674B2

Reaction notes

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