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

HRID 12423

Reaction equation

HRID 12423 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-84c3e5202db24794ad5e0005d8f79a15
Source dataset
uspto-grants-2010_06
Patent number
US07728013B2

Linked notes

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