HCID 58170483, compound → 6-Bromo-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

HRID 1619118Notes

Reaction equation

HRID 1619118 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:29]([O-])=O)[C:5]([CH:8](C(OCC2C=CC=CC=2)=O)[C:9](OCC2C=CC=CC=2)=[O:10])=[N:6][CH:7]=1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]2[NH:29][C:9](=[O:10])[CH2:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 58170483HCID 58170483, compound

Product 1

HCID 469416416-Bromo-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-oneYield 54%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

Iron dust (0.82 g, 14.60 mmol) was added to a solution of dibenzyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (preparation 30b, 1.78 g, 3.70 mmol) in glacial acetic acid (50 mL) and the mixture was heated with stirring to 120° C. After 7 hours, the mixture was cooled and left to stand overnight. The reaction was poured onto ice-water and extracted first with ethyl acetate and then with chloroform. The combined organic extract was washed with brine, dried (MgSO4) and evaporated in vacuo. Purification of the residue by flash chromatography (98:2 dichloromethane/methanol) gave the title compound (0.42 g, 54%) as a pink solid.

Workup

  1. temperaturethe mixture was heated
  2. temperaturethe mixture was cooled
  3. waitleft
  4. waitto stand overnight
  5. additionThe reaction was poured onto ice-water
  6. extractionextracted first with ethyl acetate
  7. extractionThe combined organic extract
  8. washwas washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo
  11. customPurification of the residue by flash chromatography (98:2 dichloromethane/methanol)

Sources & evidence

ORD record
ord-e0021141d6d1470cba48d4cbfb7b5c28
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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