Acetic Acid → 7-Azaoxindole acetic acid salt

HRID 24401Notes

Reaction equation

HRID 24401 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[C:13]([OH:16])(=[O:15])[CH3:14]>C(#N)C.[Zn]>[C:13]([OH:16])(=[O:15])[CH3:14].[NH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:2][C:3]1=[O:11]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 138640943,3-Dibromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

Product 1

HCID 219257347-Azaoxindole acetic acid saltYield 91%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6342AcetonitrileSolvent

Procedure

Zinc dust (6.5 g) was added to a solution of 3,3-dibromo-7-azaoxindole (2.9 g) in acetic acid (20 ml) and acetonitrile (30 ml). The mixture was stirred for 2 hours at room temperature. The solids were removed by filtration and the solvent evaporated. The residue was treated with ethyl acetate. The ethyl acetate solution containing insoluble solid was passed through a short column of silica gel. The collected ethyl acetate solution was evaporated and the residue dried under vacuum to give 1.8 g (91% yield) of 7-aza-2-oxindole acetic acid salt.

Workup

  1. customThe solids were removed by filtration
  2. customthe solvent evaporated
  3. additionThe residue was treated with ethyl acetate
  4. additionThe ethyl acetate solution containing insoluble solid
  5. customThe collected ethyl acetate solution was evaporated
  6. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-72dacf05edc84f9095ba6d710f037b89
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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