Benzenesulfonyl chloride → HCID 68716389, compound

HRID 1159778Notes

Reaction equation

HRID 1159778 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH3:13])=[CH:7][NH:8]2.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH3:13])=[CH:7][N:8]2[S:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 529877044-Bromo-3-methyl-1H-indole3×

Product 1

HCID 68716389HCID 68716389, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Aq. 4M NaOH (3 mL) was added to a stirring mixture of 4-bromo-3-methyl-1H-indole (456 mg, 2.17 mmol; Intermediate 28), benzenesulfonyl chloride (306 μg, 2.39 mmol) and tetrabutylammonium hydrogen sulfate (74 mg, 0.22 mmol) in DCM (30 mL). The reaction mixture was stirred 1 h, combined with an earlier batch of this intermediate (followed this experimental and starting with 4-bromo-3-methyl-1H-indole, 100 mg, 0.48 mmol; Intermediate 28), washed twice with water, dried and concentrated. The crude product was purified by flash column chromatography (DCM/hexane 1:3). The product (650 mg, 70%) was obtained as a white solid. MS (ESI+) for C15H12BrNO2S m/z 350 (Monoisotop+H)+.

Workup

  1. washIntermediate 28), washed twice with water
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product was purified by flash column chromatography (DCM/hexane 1:3)

Sources & evidence

ORD record
ord-c72d1a5015124a7681370aa87a398b4c
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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