Benzenesulfonyl chloride → 6-Chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 889585Notes

Reaction equation

HRID 889585 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)(=O)C>C1COCC1>[C:13]1([S:19]([N:8]2[C:9]3=[N:10][C:2]([Cl:1])=[CH:3][CH:4]=[C:5]3[CH:6]=[CH:7]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 113441186-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 497590336-Chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6-Chloro-7-azaindole (9.3 g, 61.1 mmol), prepared as described (Synthesis, 1992), was dissolved in 100 ml anhydrous THF under N2. At 0° C., a 60% dispersion of NaH 3.5 g (65.9 mmol) in mineral oil was added. After stirring for 1 hour at room temperature, the mixture was cooled (0° C.) and 8.7 ml (67.2 mmol) benzenesulfonyl chloride dissolved in 20 ml anhydrous THF was added. The reaction mixture was stirred at room temperature for 1 hour. Ethyl acetate was added to the mixture and the organic layer was washed three times with a saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography (diethyl ether/PE gradient (1:4 to pure diethyl ether) to give 1-benzenesulfonyl-6-chloro-1H-pyrrolo[2,3-b]pyridine (amorphous, 14.4 g, 80.7%) (TLC diethyl ether/PE (1/1) Rf 0.37). LCMS; Rt: 1.98 min, ([M+H]+=293).

Workup

  1. custom(Synthesis, 1992)
  2. additionwas added
  3. stirringThe reaction mixture was stirred at room temperature for 1 hour
  4. washthe organic layer was washed three times with a saturated NaHCO3 solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (diethyl ether/PE gradient (1:4 to pure diethyl ether)

Sources & evidence

ORD record
ord-93a14706e62c42a9bd259db53b0d480e
Source dataset
uspto-grants-2012_08
Patent number
US08252930B2

Reaction notes

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