Potassium Carbonate → HCID 45787718, compound

HRID 2191906Notes

Reaction equation

HRID 2191906 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CN1CCCC1=O>[Br:8][C:4]1[N:3]=[C:2]([N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[O:9])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 516892Sodium BicarbonateHCID 178516071HCID 178516071, compound

Product 1

HCID 45787718HCID 45787718, compoundYield 32.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2,6-dibromopyridine (4.74 g), 2-hydroxypyridine (2.85 g), potassium carbonate (4.15 g) and N-methylpyrrolidone (1 mL) were stirred at 150° C. for 6 hours. The reaction solution was cooled to room temperature, then ethyl acetate and aqueous sodium hydrogencarbonate solution were added thereto, the insoluble matter was removed through Celite filtration, and the organic layer was separated. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to give the entitled compound as a white solid (1.63 g).

Workup

  1. customthe insoluble matter was removed through Celite filtration
  2. customthe organic layer was separated
  3. washThis was washed with saturated saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. customThe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c0e7b6192f52498c8c84025a6a309edd
Source dataset
uspto-grants-2012_12
Patent number
US08329711B2

Reaction notes

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