Ethyl bromoacetate → HCID 8027287, compound

HRID 1056660Notes

Reaction equation

HRID 1056660 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=CN=1.[CH2:8]([O:10][C:11](=[O:14])[CH2:12]Br)C.C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O>[CH3:8][O:10][C:11](=[O:14])[CH2:12][C@@H:2]1[CH2:7][CH2:6][CH2:5][O:1]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 178516071HCID 178516071, compound

Product 1

HCID 8027287HCID 8027287, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of hydroxy-pyridine 42d (1.5g, 5.6 mmol), ethylbromoacetate (0.95 mL, 8.4 mmol) and Na2CO3 (0.93 mg, 8.8 mmol) is refluxed (75° C.) in acetone (35 mL) for 6 h. The solution is concentrated, then diluted with H2O/DCM. The aqueous phase is extracted with DCM. The combined organic extracts are washed with brine, dried (MgSO4) and concentrated. Purification by chromatography (20-100% EtOAc in hexanes) afford affords ester 42e.

Workup

  1. concentrationThe solution is concentrated
  2. additiondiluted with H2O/DCM
  3. extractionThe aqueous phase is extracted with DCM
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (20-100% EtOAc in hexanes)
  8. customafford

Sources & evidence

ORD record
ord-4f97ce741ca74a7a9e1fa431538b23db
Source dataset
uspto-grants-2016_07
Patent number
US09399645B2

Reaction notes

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