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

HRID 1820875Notes

Reaction equation

HRID 1820875 reaction equation
[Br: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>CC(C)=O>[C:17]1([S:23]([N:4]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:10]3[C:2]([Br:1])=[CH:3]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 55236593-Bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 455881343-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Bromo-1H-pyrrolo[2,3-b]pyridine (3, 280 mg, 1.4 mmol) was dissolved in acetone (15 mL) and potassium carbonate (220 mg, 1.6 mmol) was added, followed by benzenesulfonyl chloride (0.2 mL, 1.6 mmol). The reaction mixture was heated to reflux overnight, filtered and concentrated under reduced pressure. The resulting solid was purified by flash chromatography (5%-20% ethyl acetate:hexanes) to provide the desired product, 4, (300 mg, 47%). MS(ESI) [M+H+]+=455.0.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting solid was purified by flash chromatography (5%-20% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-03f70001f2d7404e91a8c67edb3850e5
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

Loading…