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

HRID 1072126Notes

Reaction equation

HRID 1072126 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].C(O)(=O)C.CO>[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

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 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)-oneYield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 3,3-dibromo-4-chloro-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (0.745 g, 2.3 mmol), zinc dust (1.49 g, 23 mmol), acetic acid (10 mL) and methanol (10 mL) was stirred at room temperature for 2 hours. The reaction mixture was then diluted with brine and extracted with ethyl acetate. The organic layer was further washed with brine, dried over anhydrous sodium sulfate, concentrated and dried in a vacuum oven to give 0.3 g (78%) of 4-chloro-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one as a tan solid. 1H NMR (360 MHz, DMSO-d6) δ 11.21 (s, br, NH), 8.01 (d, J=5.66 Hz, 1H), 7.23 (d, J=5.66 Hz, 1H), and 3.59 (s, 2H, CH2). MS m/e 168 [M+].

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was further washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-8ec6c593e5584d2d9a31eb6aefcc8d90
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Reaction notes

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