Methyl iodide → Ethyl 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylate

HRID 1472612Notes

Reaction equation

HRID 1472612 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:19])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][NH:12][CH:13]=2)=[CH:4][CH:3]=1.IC.[C:22]([O-])(O)=O.[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:19])[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][N:12]([CH3:22])[CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 68009264Ethyl 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylateYield 69.9%

Procedure

A mixture of Example A7 (1.5 g, 5.7 mmol) and iodomethane (0.9 g, 6.3 mmol) in satd. NaHCO3 (25 mL) was heated at 60° C. overnight. The mixture was filtered. The solid was concentrated under vacuum to afford ethyl 5-(4-fluorophenyl)-1-methyl-4-oxo-1,4-dihydropyridine-3-carboxylate (1.1 g, 69.9% yield) which was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationThe solid was concentrated under vacuum

Sources & evidence

ORD record
ord-8a819613f3d54ea5aee64c24c32bf6cb
Source dataset
uspto-grants-2015_04
Patent number
US09012635B2

Reaction notes

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