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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 910607Generated: October 31, 2026

Sodium Carbonate → Methyl 4-(1-methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoate

https://huagongshe.com/reaction/910607

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant4-Methoxycarbonylphenylboronic acidHCID 2734369—
Reactant3-Bromo-1-methylpyridin-4(1H)-one hydrobromideHCID 67391229—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
ProductMethyl 4-(1-methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoateHCID 5758398720.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

3-Bromo-1-methylpyridin-4(1H)-one hydrobromide (640 mg) was suspended in toluene (10 ml) and water (5 ml), and [4-(methoxycarbonyl)phenyl]boronic acid (642 mg), sodium carbonate (757 mg) and tetrakis(triphenylphosphine)palladium(0) (138 mg) were added, followed by stirring under heating in an oil bath at 100° C. for 3 hours. The reaction mixture was filtered through Celite, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL Ltd., the same shall apply hereinunder) (chloroform:methanol=90:10) to obtain methyl 4-(1-methyl-4-oxo-1,4-dihydropyridin-3-yl)benzoate (118 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08022208B2
Source datasetuspto-grants-2011_09
ORD IDord-d8dadfb36d564b3787e009425b8e300a
Source noteuspto-grants-2011_09