Potassium Carbonate → Methyl 4-((5-chloro-6-isobutoxypyridin-3-yloxy)methyl)-3-methoxybenzoate

HRID 512058Notes

Reaction equation

HRID 512058 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].[Cl:21][C:22]1[CH:23]=[C:24]([OH:33])[CH:25]=[N:26][C:27]=1[O:28][CH2:29][CH:30]([CH3:32])[CH3:31]>CC(C)=O>[Cl:21][C:22]1[CH:23]=[C:24]([O:33][CH2:2][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=2[O:13][CH3:14])[CH:25]=[N:26][C:27]=1[O:28][CH2:29][CH:30]([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 580425005-Chloro-6-isobutoxypyridin-3-OL

Product 1

HCID 66667869Methyl 4-((5-chloro-6-isobutoxypyridin-3-yloxy)methyl)-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 4-(bromomethyl)-3-methoxybenzoate (250 mg, 0.965 mmol) in acetone (20.0 mL) were added potassium carbonate (267 mg, 1.93 mmol) and 5-chloro-6-isobutoxypyridin-3-ol (Preparation 1, 195 mg, 0.965 mmol) and the reaction mixture was heated at reflux for 16 hours, then allowed to cool to room temperature. The solvent was removed in vacuo to yield a yellow solid, which was partitioned between EtOAc (30.0 mL) and water (50.0 mL). The aqueous was further extracted with EtOAc (2×30 mL). The combined organics were washed with sodium hydroxide solution (1 M, 30 mL) then brine (50 mL), dried over sodium sulfate and the solvent was removed in vacuo to yield the title compound as a pale yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed in vacuo
  4. customto yield a yellow solid, which
  5. customwas partitioned between EtOAc (30.0 mL) and water (50.0 mL)
  6. extractionThe aqueous was further extracted with EtOAc (2×30 mL)
  7. washThe combined organics were washed with sodium hydroxide solution (1 M, 30 mL)
  8. dry with materialbrine (50 mL), dried over sodium sulfate
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-395e96328f884fedbab39eb5c5bd289f
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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