Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-4-pyrazin-2-yl-1H-indole

HRID 1159808Notes

Reaction equation

HRID 1159808 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[C:16]1([S:22]([N:11]2[C:12]3[C:8](=[C:7]([C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)[CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:10]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 687176654-pyrazin-2-yl-1H-indole2×

Product 1

HCID 687170021-(Phenylsulfonyl)-4-pyrazin-2-yl-1H-indole

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

4-Pyrazin-2-yl-1H-indole (0.060 g, 0.307 mmol, Intermediate 65), benzensulfonyl chloride (0.071 g, 0.40 mmol) and tetrabutylammonium hydrogen sulfate (0.010 g, 0.031 mmol) were dissolved in dichloromethane (3 mL) and NaOH (0.061 g, 1.5 mmol) in water (1 mL) was added. The mixture was stirred at rt overnight and the mixture was diluted with dichloromethane and water and extracted with dichloromethane (2×). The organic phase was dried (MgSO4) and evaporated. The crude product was purified by flash chromatography using CH2Cl2 to 1% MeOH in CH2Cl2 as the eluent. Yield: 81 mg (79%). White solid. MS (electronspray; [M+H]+) m/z 336.4.

Workup

  1. extractionextracted with dichloromethane (2×)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-87b331da22134b10804f6b12ed049ebd
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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