Benzenesulfonyl chloride → 3-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

HRID 1625483Notes

Reaction equation

HRID 1625483 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[Cl:11])[NH:4][CH:3]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[Cl:11])[N:4]([S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])[CH:3]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 247295703-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 497589583-Bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridineYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (2.32 g) was dissolved in anhydrous THF and cooled to 0° C., the NaH (60%, 1.2 g) was added slowly and the mixture stirred at 0° C. for 40 min. The benzenesulfonyl chloride was added, and the mixture was allowed to warm to room temperature and stirred at room temperature for 3 h. The reaction mixture was quenched with H2O, and extracted with EtOAc. The organic layer was dried over Na2SO4. Ater the solvent evaporated under reduced pressure, the residue was purified with chromatography on silica gel to give 3-bromo-4-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine: (2.63 g), yield: 71%.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 3 h
  3. customThe reaction mixture was quenched with H2O
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customAter the solvent evaporated under reduced pressure
  7. customthe residue was purified with chromatography on silica gel

Sources & evidence

ORD record
ord-0c9bbb0ff66e4c0589e92798acfaa9ef
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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