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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 56637Generated: October 26, 2026

Potassium Carbonate → 4-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine

https://huagongshe.com/reaction/56637

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant(2-Methoxypyridin-4-yl)boronic acidHCID 23546919—
Reactant2-Bromo-4-chloro-1-[2-(trimethylsilyl)ethynyl]benzeneHCID 102078595—
Solvent1,4-DioxaneHCID 31275—
Product4-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridineHCID 123388929—

Reaction Steps

A solution of 333 mg (1.16 mmol) of [(2-bromo-4-chlorophenyl)ethynyl](trimethyl)silane, 195 mg (1.28 mmol, 1.1 eq.) of (2-methoxypyridin-4-yl)boronic acid, 401 mg (2.9 mmol, 2.5 eq.) of potassium carbonate and 14 mg (0.02 mmol, 0.015 eq.) of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/monodichloromethane adduct in 18 ml of dioxane was irradiated in a microwave at 130° C. for 15 min. The reaction mixture was then filtered through Celite and the residue was washed with dioxane. The combined filtrates were concentrated under reduced pressure. After addition of water/ethyl acetate and phase separation, the organic phase was concentrated under reduced pressure. Yield: 550 mg (purity 41%, 62% of theory)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09434690B2
Source datasetuspto-grants-2016_09
ORD IDord-9bdb4e2f02ed4cfaba6cf5dfe78e68af
Source noteuspto-grants-2016_09