Acetic Acid → 4-Chloro-1H-pyrrolo[2,3-B]pyridin-2(3H)-one

HRID 911198Notes

Reaction equation

HRID 911198 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[Cl:11])[NH:4][C:3]1=[O:12].CC(O)=O.CO.CCOC(C)=O>[Cl-].[Na+].O.[Zn]>[Cl:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:4][C:3](=[O:12])[CH2:2][C:10]=12

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 8857Ethyl AcetateHCID 223909813,3-Dibromo-4-chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

Product 1

HCID 111945634-Chloro-1H-pyrrolo[2,3-B]pyridin-2(3H)-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

The title compound was prepared according to the procedure described in WO2001046196A 1. A mixture of 3,3-dibromo-4-chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (4.07 g, 12.5 mmol), zinc dust (8.15 g, 125 mmol), AcOH (54.2 ml, 12.5 mmol), and MeOH (54.2 ml, 12.5 mmol) was stirred at rt. After 3 h, the reaction mixture was passed through a pad of celite with an aid of EtOAc. The filtrate was then diluted with brine. The whole was extracted with EtOAc. The organic layer was further washed with brine, dried over MgSO4, filtered, concentrated. The product was purified by column chromatography on silica gel using 70:30 DCM:(90:10:1 DCM:MeOH:NHOH). Fractions containing the product were concentrated. White cotton-like solid, 4-chloro-1H-pyrrolo[2,3-b]pyridin-2(3H)-one was obtained. MS Calcd for C7H5ClN2O: [M]+=168. Found: [M+H]+=169.

Workup

  1. customThe title compound was prepared
  2. extractionThe whole was extracted with EtOAc
  3. washThe organic layer was further washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography on silica gel using 70:30 DCM
  8. additionFractions containing the product
  9. concentrationwere concentrated

Sources & evidence

ORD record
ord-c3e7a634a8d0454281389d69a67bc84c
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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