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 1361959Notes

Reaction equation

HRID 1361959 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-oneYield 32%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 3,3,5-tribromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (2.0 g, 5.4 mmole) in acetic acid (50 mL) at RT was added Zn metal. The reaction became exothermic and was cooled by the use of an ice bath during the initial 30 minutes. After 5 hr the reaction was filtered through Celite®, and the filter pad was washed with EtOAc. The filtrate was concentrated under vacuum and neutralized with saturated aqueous NaHCO3 solution. The neutralized aqueous filtrate was then extracted with EtOAc (2×200 mL), and the combined organic extracts were dried over Na2SO4 and concentrated to a solid. The solid was washed with hexanes and dried under high vacuum to give the title compound (0.36 g, 32%): MS (ES) m/e 215 (M+H)+. This was used without further purification.

Workup

  1. temperaturewas cooled by the use of an ice bath during the initial 30 minutes
  2. filtrationAfter 5 hr the reaction was filtered through Celite®
  3. washthe filter pad was washed with EtOAc
  4. concentrationThe filtrate was concentrated under vacuum
  5. extractionThe neutralized aqueous filtrate was then extracted with EtOAc (2×200 mL)
  6. dry with materialthe combined organic extracts were dried over Na2SO4
  7. concentrationconcentrated to a solid
  8. washThe solid was washed with hexanes
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-bd84ffebe2c54c74bca54d017a294607
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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