Acetic Acid → 7-Azaoxindole acetic acid salt

HRID 1243392Notes

Reaction equation

HRID 1243392 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

3,3-Dibromo-7-azaoxindole (2.9 g) was dissolved in a mixture of 20 mL of acetic acid and 30 mL of acetonitrile. To the solution was added 6.5 g of zinc dust. The mixture was stirred for 2 hrs at room temperature. The solid was filtered from the mixture and the solvent evaporated. The residue was slurried 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 (yield 91%) of 7-azaoxindole acetic acid salt.

Workup

  1. filtrationThe solid was filtered from the mixture
  2. customthe solvent evaporated
  3. additionThe ethyl acetate solution containing insoluble solid
  4. customThe collected ethyl acetate solution was evaporated
  5. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-78b1ed2023f44fe6b0b95536a695f5ae
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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