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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1916731Generated: October 26, 2026

Sodium Carbonate → 1-(2-{4-[4-(4-Chloro-phenyl)-thiophen-2-ylethynyl]-phenoxy}-ethyl)-pyrrolidine

https://huagongshe.com/reaction/1916731

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactantp-Chlorophenylboric acidHCID 17810664—
Reactant1-{2-[4-(4-Bromo-thiophen-2-ylethynyl)-phenoxy]-ethyl}-pyrrolidineHCID 67362306—
Solvent1,4-DioxaneHCID 31275—
Product1-(2-{4-[4-(4-Chloro-phenyl)-thiophen-2-ylethynyl]-phenoxy}-ethyl)-pyrrolidineHCID 59835810—

Reaction Steps

Under an N2 atmosphere 5 mL 2 M Na2CO3 solution and 47 mg (0.41 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 310 mg (0.82 mmol) 1-{2-[4-(4-bromo-thiophen-2-ylethynyl)-phenoxy]-ethyl}-pyrrolidine and 129 mg (0.82 mmol) 4-chlorophenyl-boric acid in 10 mL 1,4-dioxane and the reaction mixture is refluxed for 1 h. The hot solution is filtered through a fibreglass filter, the filtrate is extracted with EtOAc, the organic phase is washed with water and dried over MgSO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 8:2:0.2).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618132B2
Source datasetuspto-grants-2013_12
ORD IDord-7a66d1913d8645b48f56571fd4e0050e
Source noteuspto-grants-2013_12