Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-4-chloro-5-azaindole

HRID 651645Notes

Reaction equation

HRID 651645 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[Cl:13][C:14]1[C:19]2[CH:20]=[CH:21][NH:22][C:18]=2[CH:17]=[CH:16][N:15]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:1]1([S:7]([N:22]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([Cl:13])[C:19]=3[CH:20]=[CH:21]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 141143844-chloro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 181764061-(Phenylsulfonyl)-4-chloro-5-azaindoleYield 70.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Benzenesulfonyl chloride (3 mL, 23.5 mmol) is added dropwise to a solution of tetrabutylammonium hydrogen sulfate (0.53 g, 1.56 mmol), sodium hydroxide (1.56 g, 38.9 mmol) and 4-chloro-1H-pyrrolo[3,2-c]pyridine (2.38 g, 15.6 mmol) (prepared according to Rasmussen, M. J. Het. Chem, 1992, 29, 359) in CH2Cl2. The mixture is stirred at room temperature for 4 hours the diluted with CH2Cl2 and washed with saturated NH4Cl solution and brine. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with 1% MeOH/CH2Cl2 to 2% MeOH/CH2Cl2 to afford the title product (3.21 g, 11 mmol) as a white solid.

Workup

  1. washwashed with saturated NH4Cl solution and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography
  6. washeluting with 1% MeOH/CH2Cl2 to 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-15edfa8c9cf94e179fbe522fe0434ff0
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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