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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 228784Generated: October 26, 2026

Dimethylformamide → 4-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenol

https://huagongshe.com/reaction/228784

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
Reactant4-Hydroxyphenylboronic acidHCID 2734360—
Reactant4-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinolineHCID 10093673—
SolventWaterHCID 962—
Product4-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenolHCID 13613162075%

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-hydroxyphenylboronic acid (81 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 (34 mg, yield 75%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07560558B2
Source datasetuspto-grants-2009_07
ORD IDord-bc64bc4c5f984b1a847fe633b9020650
Source noteuspto-grants-2009_07