Ethyl bromoacetate → Ethyl (1H-pyrazolo[3,4-b]pyridin-1-yl)acetate

HRID 82195Notes

Reaction equation

HRID 82195 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[N:2]1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][N:1]1[C:9]2=[N:8][CH:7]=[CH:6][CH:5]=[C:4]2[CH:3]=[N:2]1)[CH3:16]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 27558501H-pyrazolo(3,4-b)pyridine

Product 1

HCID 57642798Ethyl (1H-pyrazolo[3,4-b]pyridin-1-yl)acetateYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 7-aza indazole (250 mg, 2.1 mmol) and ethyl bromoacetate (0.47 mL, 4.2 mmol) in DMF (8 mL) was added K2CO3 (1.16 gm, 8.4 mmol) and the resulting mixture stirred at 70° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). The organic layer was washed with water (2×5 mL), brine (5 mL), dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified using silica gel column chromatography eluting with EtOAc:hexane 10:90 to afford the title compound as an off-white solid in 49% yield, 210 mg.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with water (2×5 mL), brine (5 mL)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified
  7. washeluting with EtOAc:hexane 10:90

Sources & evidence

ORD record
ord-794e1543a55d4c98b01bac4bcb6cc64f
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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