Sodium Hydroxide → HCID 68717330, compound

HRID 1159766Notes

Reaction equation

HRID 1159766 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.[F:13][C:14]([F:26])([F:25])[C:15]1[CH:16]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:21]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:25])[F:26])[CH:16]=1)(=[O:23])=[O:22]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 6764944-BromoindoleHCID 27332503-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 68717330HCID 68717330, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Aq. 2.5M NaOH (5 mL) was added to a stirring mixture of 4-bromo-1H-indole (1000 mg, 5.3 mmol), 3-(trifluoromethyl)benzenesulfonyl chloride (1300 mg, 5.6 mmol) and tetrabutylammonium hydrogen sulfate (173 mg, 0.5 mmol) in DCM (10 mL). The reaction mixture was stirred at ambient temperature overnight. The mixture was diluted with DCM and water and the layers were separated. DCM was washed with water 2 times, dried (MgSO2) and concentrated to give 1.6 g of crude material that was purified using flash chromatography (SiO2, eluent EtOAc:hexane 9:1) giving the title product (0.91 g, 44%).

Workup

  1. customthe layers were separated
  2. washDCM was washed with water 2 times
  3. dry with materialdried (MgSO2)
  4. concentrationconcentrated
  5. customto give 1.6 g of crude material that
  6. customwas purified

Sources & evidence

ORD record
ord-cbf55be20cab441c92340d70ade2a645
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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