3,3,5-Tribromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one → 5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

HRID 2298766Notes

Reaction equation

HRID 2298766 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Br:11])[CH:9]=2)[NH:4][C:3]1=[O:12]>C(O)(=O)C.[Zn]>[Br:11][C:8]1[CH:9]=[C:10]2[CH2:2][C:3](=[O:12])[NH:4][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 219561923,3,5-Tribromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

Product 1

HCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Under argon at room temperature, 17.60 g (0.27 mol) of powdered zinc are added in portions to 5 g (13.5 mmol) of the compound obtained in Step A dissolved in 100 ml of acetic acid. After 15 hours' stirring at room temperature, the acetic acid is removed by evaporation under reduced pressure (coevaporation with toluene). The residue, which is taken up in ethyl acetate, is washed once with water; the aqueous phase is washed several times with ethyl acetate. The organic phases are combined, dried over magnesium sulphate, concentrated and purified by flash chromatography over silica gel (eluant: dichloromethane/methanol, 95/5), to obtain the title compound in the form of an orange solid.

Workup

  1. customthe acetic acid is removed by evaporation under reduced pressure (coevaporation with toluene)
  2. washis washed once with water
  3. washthe aqueous phase is washed several times with ethyl acetate
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. custompurified by flash chromatography over silica gel (eluant: dichloromethane/methanol, 95/5)

Sources & evidence

ORD record
ord-85472d327627441faf7de5d52262f5ab
Source dataset
uspto-grants-2002_12
Patent number
US06495543B1

Reaction notes

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