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

HRID 2361104Notes

Reaction equation

HRID 2361104 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 WO2001046196A1. 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:NH4OH). 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-c78af1f07d164797b0fa6e32d73f592c
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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