Acetic Acid → 2-oxo-1H,2H,3H-pyrrolo[2,3-b]pyridine-4-carbonitrile

HRID 888125Notes

Reaction equation

HRID 888125 reaction equation
Br[C:2]1(Br)[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[N:6][C:5]=2[NH:4][C:3]1=[O:13].CC(O)=O>CC#N.[Zn]>[O:13]=[C:3]1[NH:4][C:5]2[N:6]=[CH:7][CH:8]=[C:9]([C:11]#[N:12])[C:10]=2[CH2:2]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 69264126HCID 69264126, compound

Product 1

HCID 692637962-oxo-1H,2H,3H-pyrrolo[2,3-b]pyridine-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3,3-dibromo-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (4 g) in CH3CN (75 mL) was added AcOH (2 mL) followed by Zinc dust (4, 63 mmol). Mixture was stirred for 2 h at RT and was filtered. Solvent was evaporated and MeOH was added. A solid precipitated, which was filtered and dried.

Workup

  1. filtrationwas filtered
  2. customSolvent was evaporated
  3. additionMeOH was added
  4. customA solid precipitated
  5. filtrationwhich was filtered
  6. customdried

Sources & evidence

ORD record
ord-827029395fb14d1cb8aec7a5b996de41
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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