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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 228694Generated: October 27, 2026

Water → 4-(4,5-Dimethyl-2-pyridin-3-yl-phenoxy)-6,7-dimethoxy-quinoline

https://huagongshe.com/reaction/228694

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantPotassium CarbonateHCID 11430—
Reactant3-Pyridinylboronic acidHCID 2734378—
Reactant4-(2-Iodo-4,5-dimethyl-phenoxy)-6,7-dimethoxyquinolineHCID 23078361—
SolventDimethylformamideHCID 6228—
Product4-(4,5-Dimethyl-2-pyridin-3-yl-phenoxy)-6,7-dimethoxy-quinolineHCID 2307827325%

Reaction Conditions

Temperature100 °C

Reaction Steps

4-(2-Iodo-4,5-dimethyl-phenoxy)-6,7-dimethoxyquinoline (compound 164) (59 mg), pyridine-3-boronic acid (33 mg), and tetrakistriphenylphosphine palladium (10 mg) were dissolved in N,N-dimethylformamide (4 ml), a 2 M aqueous potassium carbonate solution (0.5 ml) was added to the reaction system, and the mixture was stirred at 100° C. for 30 min. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (13 mg, yield 25%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07560558B2
Source datasetuspto-grants-2009_07
ORD IDord-015b3acdc79b4be191c997307d8b5d49
Source noteuspto-grants-2009_07