Water → 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 893374Notes

Reaction equation

HRID 893374 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>O1CCCC1>[C:12]1([S:18]([N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[CH:3]=[CH:2]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24758Sodium hydride

Product 1

HCID 8520781-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of pyrrolo[2,3-b]-pyridine (1.0 g, 8.46 mmol) in tetrahydrofuran (15 mL) at room temperature (rt) was added NaH (280 mg of an 80% dispersion in oil, 9.31 mmol) in portions. After 20 min the solution was cooled to 0° C. and benzenesulfonyl chloride (1.13 mL, 8.88 mmol) was added over 10 min. After 30 min the reaction mixture was warmed to rt and stirred for 1 h. Water (30 mL) was added and the mixture was extracted with EtOAc (40 mL). The organic layer was washed with 5% aqueous NaHCO3 then dried (MgSO4). Concentration and crystallization from EtOAc-hexanes gave 1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine as a solid.

Workup

  1. temperatureAfter 30 min the reaction mixture was warmed to rt
  2. extractionthe mixture was extracted with EtOAc (40 mL)
  3. washThe organic layer was washed with 5% aqueous NaHCO3
  4. dry with materialthen dried (MgSO4)
  5. concentrationConcentration and crystallization from EtOAc-hexanes

Sources & evidence

ORD record
ord-a08f23312bcf4893904c7589ec119b1a
Source dataset
uspto-grants-1992_06
Patent number
US05124335

Reaction notes

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