Ethyl bromoacetate → HCID 8027287, compound

HRID 1056657Notes

Reaction equation

HRID 1056657 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]N=1.[C:8](=[O:11])([O-])[O-:9].[K+].[K+].Br[CH2:15]C(OCC)=O>CC(C)=O>[CH3:15][O:9][C:8](=[O:11])[CH2:4][C@@H:5]1[CH2:6][CH2:7][CH2:2][O:1]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178516071HCID 178516071, compound

Product 1

HCID 8027287HCID 8027287, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of crude hydroxy-pyridine 21c (4.92 g, 21.1 mmol) in acetone is added potassium carbonate (4.36 g, 31.6 mmol) and ethyl bromoacetate (3.5 mL, 31.6 mmol). The mixture is refluxed for 1 h, then quenched with water and extracted with EtOAc. The combined organic layers are washed with brine, dried (Na2SO4), filtered and concentrated to provide crude ester 21d, which is used as such in the next step.

Workup

  1. temperatureThe mixture is refluxed for 1 h
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8e7587ee62c1451585c04f4051dedf7b
Source dataset
uspto-grants-2016_07
Patent number
US09399645B2

Reaction notes

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