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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 228782Generated: October 26, 2026

Dimethylformamide → 1-{4-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl}-ethanone

https://huagongshe.com/reaction/228782

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
Reactant4-Acetylphenylboronic acidHCID 3702122—
Reactant4-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinolineHCID 10093673—
SolventWaterHCID 962—
Product1-{4-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenyl}-ethanoneHCID 5775647953%

Reaction Conditions

Temperature70 °C

Reaction Steps

N,N-Dimethylformamide (1 ml) and a 2 M aqueous potassium carbonate 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 (14 mg), and 4-acetylphenylboronic acid (97 mg) under an argon atmosphere, and the mixture was stirred at 70° C. overnight. The reaction solution was cooled to room temperature, water was then added thereto, 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 by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (26 mg, yield 52%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07560558B2
Source datasetuspto-grants-2009_07
ORD IDord-1bc711a4143e49b6b415b8ab1bd9aa09
Source noteuspto-grants-2009_07