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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1528094Generated: October 30, 2026

Sodium Carbonate → 1-(6-(3,6-Dihydro-2H-pyran-4-yl)pyridin-2-yl)-3-(8-fluoroquinolin-4-yl)urea

https://huagongshe.com/reaction/1528094

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant3,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 11218053—
Reactant1-(8-Fluoroquinolin-4-yl)-3-(6-iodopyridin-2-yl)ureaHCID 86667493—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
SolventDimethylformamideHCID 6228—
Product1-(6-(3,6-Dihydro-2H-pyran-4-yl)pyridin-2-yl)-3-(8-fluoroquinolin-4-yl)ureaHCID 5752126323.6%

Reaction Conditions

Temperature80 °C

Reaction Steps

1-(8-Fluoroquinolin-4-yl)-3-(6-iodopyridin-2-yl)urea (250 mg, 0.582 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (187 mg, 0.873 mmol), sodium carbonate solution (2M, 1.31 mL, 2.62 mmol) and tetrakis(triphenylphosphine)-palladium(0) (68 mg, 0.058 mmol) were dissolved in 5 ml of DMF under an argon atmosphere and the mixture was stirred at 80° C., in a microwave oven, for one hour. After the solvent had been evaporated down to dryness, the resulting residue was treated with water and the mixture was then extracted with ethyl acetate. After the combined organic phases had been dried over sodium sulfate and the solvent had been filtered and evaporated down to dryness, the resulting residue was purified by column chromatography to give the title product (50 mg, 19%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09090592B2
Source datasetuspto-grants-2015_07
ORD IDord-54f77c36cfe74601865aace10a9570f1
Source noteuspto-grants-2015_07