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

HRID 2196666Notes

Reaction equation

HRID 2196666 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:25])=[O:24])[CH:3]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 53770783-Iodo-7-azaindole

Product 1

HCID 242292281-(Benzenesulfonyl)-3-iodo-1H-pyrrolo[2,3-b]pyridineYield 74.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Iodo-1H-pyrrolo[2,3-b]pyridine (4.55 g, 18.7 mmol) and K2CO3 (7.73 g, 55.9 mmol) were dissolved in acetonitrile (200 mL). Benzenesulfonyl chloride (4.76 mL, 37.3 mmol) was added, and the reaction mixture was heated to reflux for 10 hours. The reaction mixture was cooled and partitioned between EtOAc and water. The organic layer was washed with water (2×), brine, and dried over Na2SO4 and concentrated. The resulting residue was purified by column chromatography (4:1 to 0:1 hexane/DCM) giving 3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (5.31 g, 74.1%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 10 hours
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned between EtOAc and water
  5. washThe organic layer was washed with water (2×), brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography (4:1 to 0:1 hexane/DCM)

Sources & evidence

ORD record
ord-68f713d2f14940bab3e78fcb961bd449
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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