Potassium Carbonate → HCID 59418698, compound

HRID 2178269Notes

Reaction equation

HRID 2178269 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[Br:11][C:12]1[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[C:15]([OH:22])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:11][C:12]1[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[C:15]([O:22][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 22175135Methyl 6-bromo-3-hydroxypicolinate

Product 1

HCID 59418698HCID 59418698, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Methoxybenzyl bromide (0.095 g, 0.47 mmol) was added dropwise to a suspension of methyl 6-bromo-3-hydroxypicolinate (26B) (0.100 g, 0.43 mmol) and K2CO3 (0.089 g, 0.65 mmol) in anhydrous acetone (2.5 mL). The reaction mixture was heated at reflux for 3.5 hours, cooled to rt, and concentrated under reduced pressure. Water was added and the mixture extracted with DCM. The organic phases were washed with 1 M NaOH, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography on silica gel eluting with a gradient of PE:EtOAc 84:16 to 72:28, to provide the desired product methyl 6-bromo-3-(4-methoxybenzyloxy)picolinate (40A).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3.5 hours
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added
  5. extractionthe mixture extracted with DCM
  6. washThe organic phases were washed with 1 M NaOH, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe concentrate was purified by column chromatography on silica gel eluting with a gradient of PE

Sources & evidence

ORD record
ord-5f73d23ae62b40a2a126710280993e7e
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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