Potassium Carbonate → 1-(4-Pyridinyl)-5-methyl-2-pyridone

HRID 401507

Reaction equation

HRID 401507 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.Cl.Br[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.N.[Cu]I>[N:14]1[CH:15]=[CH:16][C:11]([N:6]2[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]2=[O:8])=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 704822-Hydroxy-5-methylpyridineHCID 881004-Bromopyridinium chloride

Product 1

HCID 97940881-(4-Pyridinyl)-5-methyl-2-pyridone

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 222AmmoniaSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 22 was synthesized by condensation of 5-methyl-2(1H)-pyridone (327.4 mg, 3 mmol) with 4-bromopyridine hydrochloride (778 mg, 4 mmol) in the presence of CuI (60 mg, 0.3 mmol) and K2CO3 (1.36 g, 10 mmol) in DMF (3 ml) at 135° C. overnight. The reaction mixture was diluted with 10% ammonia (15 ml) and extracted with ethyl acetate. Organic extract was washed with saturated sodium chloride, dried over magnesium sulfate and evaporated. Column chromatography (5% MeOH-DCM) afforded 197 mg (35%) of the target compound as a yellowish solid. The 1H NMR spectra was consistent with the structure of Compound 22.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionOrganic extract
  3. washwas washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-20a96b4fa2614b0ba30644ffbd2d5958
Source dataset
uspto-grants-2014_06
Patent number
US08741936B2

Linked notes

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