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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1916724Generated: October 25, 2026

Sodium Carbonate → 4-[5-(4-Chloro-phenyl)-pyridin-2-yl]-2-methyl-but-3-yn-2-ol

https://huagongshe.com/reaction/1916724

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactantp-Chlorophenylboric acidHCID 17810664—
Reactant4-(5-Bromo-pyridin-2-yl)-2-methyl-but-3-yn-2-olHCID 22502471—
Solvent1,4-DioxaneHCID 31275—
Product4-[5-(4-Chloro-phenyl)-pyridin-2-yl]-2-methyl-but-3-yn-2-olHCID 69077452—

Reaction Conditions

Temperature85 °C

Reaction Steps

Under an argon atmosphere 3 mL 2 M Na2CO3 solution and 173 mg (0.15 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 720 mg (3.0 mmol) 4-(5-bromo-pyridin-2-yl)-2-methyl-but-3-yn-2-ol and 593 mg (3.6 mmol) 4-chlorophenyl-boric acid in 60 mL 1,4-dioxane and the reaction mixture is stirred for 18 h at 85° C. The mixture is evaporated down i. vac., the residue is combined with water, extracted exhaustively with EtOAc, the organic phase is washed with water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, PE/EtOAc 1:1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618132B2
Source datasetuspto-grants-2013_12
ORD IDord-3f069d70169b475c9c67d3df485d8442
Source noteuspto-grants-2013_12