Dimethyl Sulfoxide → HCID 10388190, compound

HRID 1793874Notes

Reaction equation

HRID 1793874 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[S:12]([C:15]1[CH:20]=[CH:19][C:18](F)=[CH:17][CH:16]=1)(=[O:14])=[O:13].[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CS(C)=O>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[S:12]([C:15]1[CH:20]=[CH:19][C:18]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4837PiperazineHCID 22220128HCID 22220128, compound

Product 1

HCID 10388190HCID 10388190, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

The 5-Bromo-3-(4-fluoro-benzenesulfonyl)-1-methyl-1H-indole (0.30 g, 0.85 mmol) was mixed with piperazine (0.34 g, 4 mmole) and methyl sulfoxide (3 mL). The mixture was heated at 120° C. in a sealed tube for 3 hours. The mixture was diluted with 10 mL water and the resultant precipitate was collected by filtration, washed with water, and recrystallized from chloroform/benzene to provide 5-Bromo-1-methyl-3-(4-piperazin-1yl-benzenesulfonyl)-1H-indole (0.302 g, 0.695 mmol), M+H 436.

Workup

  1. filtrationthe resultant precipitate was collected by filtration
  2. washwashed with water
  3. customrecrystallized from chloroform/benzene

Sources & evidence

ORD record
ord-455349cf17a04f76a73e9ba892ab8d49
Source dataset
uspto-grants-2006_04
Patent number
US07022708B2

Reaction notes

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