Benzenesulfonyl chloride → 5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1515847Notes

Reaction equation

HRID 1515847 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C1C=CN=CC=1.ClCCl.CN(C)C=O>[C:20]1([S:26]([N:10]2[C:7]3=[N:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]3[CH:12]=[CH:11]2)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 115211405-Nitro-7-azaindole

Product 1

HCID 497589095-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a mixture of 5-nitro-1H-pyrrolo[2,3-b]pyridine (2.0 g, 12.3 mmol), triethylamine (2.48 g, 24.6 mmol), 4-dimethylaminopyridine (0.15 g, 1.23 mmol) in dichloromethane/N,N-dimethylformamide (1:1, 60 mL) was added benzenesulfonyl chloride (3.25 g, 18.4 mmol) at 0° C. After stirring for 48 h at room temperature, the reaction was quenched with water (50 mL) and extracted with dichloromethane (2×120 mL). The organic layer was washed with a saturated sodium bicarbonate (2×30 mL), water (2×30 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 33% dichloromethane/hexanes) to afford 1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridine (2.8 g, 76%) as a yellow solid: LC/MS m/e calcd for C13H9N3O4S [M+H]+ 304.30, observed 303.9.

Workup

  1. customthe reaction was quenched with water (50 mL)
  2. extractionextracted with dichloromethane (2×120 mL)
  3. washThe organic layer was washed with a saturated sodium bicarbonate (2×30 mL), water (2×30 mL), brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 33% dichloromethane/hexanes)

Sources & evidence

ORD record
ord-282a67bd9c544d359c9a4ada44208564
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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