Benzenesulfonyl chloride → HCID 69535221, compound

HRID 1006423Notes

Reaction equation

HRID 1006423 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16]([Br:23])=[CH:17][NH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16]([Br:23])=[CH:17][N:18]3[S:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:38])=[O:37])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 23676156Sodium t-butoxideHCID 69535222HCID 69535222, compound

Product 1

HCID 69535221HCID 69535221, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 0.35 g (0.92 mmole) 4-(3-bromo-1H-indol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester in 10 mL benzene was added 0.106 g (1.1 mmole) sodium t-butoxide and 0.19 g (1.1 mmole) benzenesulfonyl chloride. The reaction mixture was stirred at room temperature for 16 hrs. The mixture was washed with 2 mL water, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to provide 0.42 g of 4-(1-benzenesulfonyl-3-bromo-1H-indol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester, m.p. 188-189°.

Workup

  1. washThe mixture was washed with 2 mL water
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-318040b7c2a94aa8bee4577051e271f6
Source dataset
uspto-grants-2004_09
Patent number
US06790848B2

Reaction notes

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