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

HRID 1515920Notes

Reaction equation

HRID 1515920 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C(N(CC)CC)C.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.ClCCl>[C:18]1([S:24]([N:8]2[C:5]3=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=[C:4]3[CH:10]=[CH:9]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 205974295-methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 497590651-(Benzenesulfonyl)-5-methyl-1H-pyrrolo[2,3-b]pyridineYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-methyl-1H-pyrrolo[2,3-b]pyridine (3.5 g, 26.5 mmol), triethylamine (8.03 g, 79.5 mmol), and 4-dimethylaminopyridine (0.32 g, 2.65 mmol) in dichloromethane (100 mL) at 0° C. was added benzenesulfonyl chloride (7.0 g, 39.8 mmol). 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 solution (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-methyl-1H-pyrrolo[2,3-b]pyridine (4.6 g, 64%) as white solid: LC/MS m/e calcd for C14H12N2O4S [M+H]+ 273.33, observed 272.9.

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 solution (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-e2552ad0ed2945e4b07fa3de07bb2c28
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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