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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 228783Generated: October 27, 2026

Toluene → {4-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl}-dimethyl-amine

https://huagongshe.com/reaction/228783

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantSodium BicarbonateHCID 516892—
Reactant4-(Dimethylamino)phenylboronic acidHCID 2734344—
Reactant4-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinolineHCID 10093673—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product{4-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl}-dimethyl-amineHCID 5775643980%

Reaction Conditions

Temperature80 °C

Reaction Steps

Toluene (1 ml), N,N-dimethylformamide (0.5 ml) and a saturated aqueous sodium hydrogencarbonate solution (0.5 ml) were added to 4-(2-iodo-6-methyl-pyridin-3-yloxy)-6,7-dimethoxy-quinoline (compound 116) (50 mg), tetrakistriphenylphosphine palladium (28 mg), and 4-dimethylaminophenylboronic acid (196 mg) under an argon atmosphere, and the mixture was stirred at 80° C. overnight. The reaction solution was cooled to room temperature, water was then added thereto, and the mixture was extracted with chloroform. The chloroform layer was then washed with water and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform-methanol to give the title compound (39 mg, yield 80%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07560558B2
Source datasetuspto-grants-2009_07
ORD IDord-cb2c83c2f70342e590e763463fb048fc
Source noteuspto-grants-2009_07