HCID 75176205, compound → 6-Chloro-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-one

HRID 1619123Notes

Reaction equation

HRID 1619123 reaction equation
Br[C:2]1(Br)[C:6]2[CH:7]=[N:8][C:9]([Cl:11])=[CH:10][C:5]=2[NH:4][C:3]1=[O:12]>C(O)(=O)C.CO.[Zn]>[Cl:11][C:9]1[N:8]=[CH:7][C:6]2[CH2:2][C:3](=[O:12])[NH:4][C:5]=2[CH:10]=1

Participants

5

Reactant 1

HCID 75176205HCID 75176205, compound

Product 1

HCID 247292216-Chloro-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-oneYield 95.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 3,3-dibromo-6-chloro-1,3-dihydro-2H-pyrrolo[3,2-c]pyridin-2-one (preparation 36d, 1.14 g, 3.49 mmol) in acetic acid (35 mL) was added zinc dust (2.23 g, 34.10 mmol) in one portion and the mixture was stirred at room temperature for 50 minutes. The mixture was diluted with methanol and filtered through a fine frit. The filtrate was evaporated under reduced pressure and the residue was purified by flash chromatography (95:5 dichloromethane/methanol) to give the title compound (0.56 g, 91%) as a white solid.

Workup

  1. filtrationfiltered through a fine frit
  2. customThe filtrate was evaporated under reduced pressure
  3. customthe residue was purified by flash chromatography (95:5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-3399c7da341b47509f28ee7f1629f686
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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