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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 269583Generated: October 25, 2026

Diethyl Ether → 2'-{5-Chloro-2-(benzyloxy)-3-pyridinyl]-3-biphenylcarboxylic acid ethyl ester

https://huagongshe.com/reaction/269583

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantPotassium CarbonateHCID 11430—
Reactant(3-Ethoxycarbonylphenyl)boronic acidHCID 3249312—
Reactant3-(2-Bromophenyl)-5-chloro-2-(benzyloxy)pyridineHCID 58730997—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventToluene ethanolHCID 21863594—
Product2'-{5-Chloro-2-(benzyloxy)-3-pyridinyl]-3-biphenylcarboxylic acid ethyl esterHCID 5873098432.6%

Reaction Conditions

Temperature70 °C

Reaction Steps

3-(2-Bromophenyl)-5-chloro-2-(benzyloxy)pyridine (80 mg, 0.214 mmol) and 3-(carbethoxy)phenylboronic acid (42 mg, 0.214 mmol) were dissolved in toluene/ethanol (1:1 1 ml) under nitrogen. Potassium carbonate (236 mg, 1.71 mmol) and tetrakis(triphenylphosphine)palladium(0) (25 mg, 0.0214 mmol) were added and the resulting mixture was heated at 70° C. in a Smithoreator® microwave for 15 minutes. After cooling, diethyl ether (5 ml) and water (5 ml) were added. The organic layer was washed with water, dried (MgSO4) and evaporated. The product was purified by flash chromatography (silica gel, 2-3% ethyl acetate:isohexane) to give the title compound as a clear oil (31 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07446222B2
Source datasetuspto-grants-2008_11
ORD IDord-94873ed2ea5842daa7af2b7cde0255bc
Source noteuspto-grants-2008_11