Potassium Carbonate → HCID 57815501, compound

HRID 385549Notes

Reaction equation

HRID 385549 reaction equation
Cl[C:2]1[C:7]([CH2:8][O:9][CH2:10][O:11][CH3:12])=[CH:6][C:5]([F:13])=[CH:4][N:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:5]1[CH:6]=[C:7]([CH2:8][O:9][CH2:10][O:11][CH3:12])[C:2]([CH3:14])=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate3×HCID 574072Trimethylboroxine3×HCID 57815340HCID 57815340, compound

Product 1

HCID 57815501HCID 57815501, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst3×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.10 g of 2-chloro-5-fluoro-3-((methoxymethoxy)methyl)pyridine in 3 mL of dioxane, 0.20 g of potassium carbonate, 68 μL of trimethylboroxin and 56 mg of tetrakis(triphenylphosphine)palladium(0) were added, and the mixture was heated under reflux while stirring for 2 hours under a nitrogen atmosphere. Thereto were added 0.20 g of potassium carbonate, 68 μL of trimethylboroxin and 56 mg of tetrakis(triphenylphosphine)palladium(0), and the mixture was heated under reflux while stirring for 2 hours under a nitrogen atmosphere. Thereto were added 0.20 g of potassium carbonate, 68 μL of trimethylboroxin and 56 mg of tetrakis(triphenylphosphine)palladium(0), and the mixture was heated under reflux while stirring for 1 hour under a nitrogen atmosphere. The insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=100:1 to obtain 93 mg of a colorless oily substance. The substance was purified by basic silica gel column chromatography using an eluent of chloroform to obtain 64 mg of 5-fluoro-3-((methoxymethoxy)methyl)-2-methylpyridine as a colorless oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperaturethe mixture was heated
  4. temperatureunder reflux
  5. stirringwhile stirring for 2 hours under a nitrogen atmosphere
  6. temperaturethe mixture was heated
  7. temperatureunder reflux
  8. stirringwhile stirring for 1 hour under a nitrogen atmosphere
  9. filtrationThe insoluble substance was filtered off
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe resultant residue was purified by silica gel column chromatography
  12. custommethanol=100:1 to obtain 93 mg of a colorless oily substance
  13. customThe substance was purified by basic silica gel column chromatography

Sources & evidence

ORD record
ord-738718cf6c7e408d935202f26f0808a4
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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