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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 228794Generated: October 27, 2026

Dimethylformamide → 6,7-Dimethoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinoline

https://huagongshe.com/reaction/228794

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant2-(Tributylstannyl)-1,3-thiazoleHCID 2763259—
Reactant4-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinolineHCID 10093673—
CatalystCopper oxideHCID 14829—
SolventWaterHCID 962—
Product6,7-Dimethoxy-4-(6-methyl-2-thiazol-2-yl-pyridin-3-yloxy)-quinolineHCID 2307857612%

Reaction Conditions

Temperature70 °C

Reaction Steps

N,N-Dimethylformamide (1 ml) was added to 4-(2-iodo-6-methyl-pyridin-3-yloxy)-6,7-dimethoxy-quinoline (compound 116) (50 mg), tetrakistriphenylphosphine palladium (14 mg), tri-n-butyl-(thiazol-2-yl)-tin (132 mg), and copper(II) oxide (1.9 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 hexane-acetone to give the title compound (5.2 mg, yield 12%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07560558B2
Source datasetuspto-grants-2009_07
ORD IDord-e1f7ba47bf014da9bb5c81357c899db6
Source noteuspto-grants-2009_07