Ammonium Chloride → 5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

HRID 840936Notes

Reaction equation

HRID 840936 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].[Cl-].[NH4+]>C1COCC1.[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

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 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 8028TetrahydrofuranSolvent

Procedure

A solution of 3,3,5-tribromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (5.0 g, 13.4 mmol) in fresh THF (100 mL) was stirred at room temperature, and a saturated aqueous solution of ammonium chloride (100 mL) was added. The flask was placed in a water bath, and activated zinc dust (15.0 g, 230 mmol) was added. The mixture was stirred for 20 min, and the zinc was removed by filtration through a pad of diatomaceous earth. The organic layer was separated, and the aqueous layer was extracted with THF (20 mL). The combined organic layers were washed with saturated brine solution and dried over anhydrous magnesium sulfate. Solvent was removed under reduced pressure. The brown residue was triturated with water (20 mL), and the tan solid was collected by filtration and dried under vacuum to give the title compound as a tan solid, 2.02 g (71%). 1H NMR (d6-DMSO) δ11.13 (s, 1H), 8.15 (s, 1H), 8.76 (s, 1H), 3.57 (s, 2H). MS (AP−ve) 211 (100) (M−H).

Workup

  1. customThe flask was placed in a water bath
  2. customthe zinc was removed by filtration through a pad of diatomaceous earth
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with THF (20 mL)
  5. washThe combined organic layers were washed with saturated brine solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customSolvent was removed under reduced pressure
  8. customThe brown residue was triturated with water (20 mL)
  9. filtrationthe tan solid was collected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-b0b766b2c5bb4a29a11ed9fee2e05a1b
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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