Sodium Carbonate → HCID 86241521, compound

HRID 2076646Notes

Reaction equation

HRID 2076646 reaction equation
[C:1](=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]([O-:18])=[O:17])O1.Cl[C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][N:28]=1>C(COC)OC.C(OCC)(=O)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:33][C:30]1[CH:31]=[CH:32][C:27]([C:22]2[CH:21]=[CH:20][C:19]([CH2:15][C:16]([O:18][CH3:1])=[O:17])=[CH:24][CH:23]=2)=[N:28][CH:29]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 8198212-Chloro-5-hydroxypyridineHCID 53423649HCID 53423649, compound

Product 1

HCID 86241521HCID 86241521, compoundYield 24%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0) (220 mg, 0.193 mmol) and a 2N aqueous sodium carbonate solution (4.63 ml) were added to a solution of methyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl(phenyl]acetate (1.07 g, 3.86 mmol) obtained in Example (12-1, and 2-chloro-5-hydroxypyridine (500 mg, 3.86 mmol) in dimethoxyethane (20 ml), and the mixture was stirred under heating with reflux overnight. The reaction mixture was diluted with ethyl acetate and water, and the insolubles were removed by filtration through Celite. After the obtained filtrate was extracted with ethyl acetate, the organic layer was washed with a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1-1/1) to give methyl [4-(5-hydroxy-2-pyridinyl)phenyl]acetate (230 mg, yield: 24%).

Workup

  1. temperatureunder heating
  2. temperaturewith reflux overnight
  3. customthe insolubles were removed by filtration through Celite
  4. extractionAfter the obtained filtrate was extracted with ethyl acetate
  5. washthe organic layer was washed with a saturated aqueous NaCl solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe residue obtained
  8. customby removing the solvent under reduced pressure
  9. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1-1/1)

Sources & evidence

ORD record
ord-0207e4daba764caf9c9b68c7818cb647
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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