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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 238299Generated: October 28, 2026

Sodium Carbonate → Methyl 3-[6-(4-fluorophenyl)pyridin-3-yl]prop-2-enoate

https://huagongshe.com/reaction/238299

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantTriphenylphosphineHCID 11776—
Reactant4-Fluorophenylboronic acidHCID 285645—
Reactant3-(6-Bromopyridin-3-yl)acrylic acid methyl esterHCID 71427582—
Catalystpalladium(II) acetateHCID 167845—
SolventEthanolHCID 702—
SolventTolueneHCID 1140—
ProductMethyl 3-[6-(4-fluorophenyl)pyridin-3-yl]prop-2-enoateHCID 68821839—

Reaction Steps

A mixture of 2980 mg (12.31 mmol) of 3-(6-bromopyridin-3-yl)acrylic acid methyl ester, 2067 mg (14.77 mmol) of 4-fluorophenylboronic acid, 138.2 mg (0.61 mmol) of palladium(II)acetate, 322.9 mg (1.23 mmol) of triphenylphosphane and 14.7 ml of a 1M sodium carbonate solution in 73 ml of toluene and 20 ml of ethanol was heated under reflux for 1.5 h. After cooling, the mixture was poured onto water and extracted with ethyl acetate. The organic phases were evaporated and residue purified by chromatography (silica gel, n-heptane/ethyl acetate 5:1). Yield: 2.4 g (76%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08642620B2
Source datasetuspto-grants-2014_02
ORD IDord-be80b9617cb04a7f8fb3a2c9e0a8cdd0
Source noteuspto-grants-2014_02