3,3-Dibromo-5-chloro-1-ethyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one → HCID 18973025, compound

HRID 2394372Notes

Reaction equation

HRID 2394372 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[N:7]([CH2:11][CH3:12])[C:6](=[O:13])[C:5]2(Br)Br>C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[N:7]([CH2:11][CH3:12])[C:6](=[O:13])[CH2:5]2

Participants

4

Reactant 1

HCID 189730903,3-Dibromo-5-chloro-1-ethyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Product 1

HCID 18973025HCID 18973025, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-chloro-3,3-dibromo-1-ethyl-7-azaoxindole (4.60 g, 13.0 mmol) in glacial acetic acid (75 mL) was added, in portions, zinc powder (2.5 g, 39 mmol). An exothermic reaction took place immediately, however, stirring at room temperature was continued for 1 hour. The mixture was poured into ice/water and then extracted with ethyl acetate. The organic extract was washed with water, dried over magnesium sulfate and evaporated to leave an oil which was chromatographed on a column of silica gel eluting with chloroform. Fractions containing the desired product were combined and concentrated in vacuo to afford an off-white solid, 1.70 g (68%). M.p. 78°-82° C.

Workup

  1. customAn exothermic reaction
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto leave an oil which
  8. customwas chromatographed on a column of silica gel eluting with chloroform
  9. additionFractions containing the desired product
  10. concentrationconcentrated in vacuo
  11. customto afford an off-white solid, 1.70 g (68%)

Sources & evidence

ORD record
ord-7f1c160c7e1b4b28b848b34c356f2b3d
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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