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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1191605Generated: November 1, 2026

Cesium carbonate → 5-{[1-(2-Chloro-3-fluoro-4-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-(hydroxymethyl)propyl]amino}-7-fluoro-1H-quinolin-2-one

https://huagongshe.com/reaction/1191605

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant5-{[(2-chloro-3-fluoro-4-methoxyphenyl)(2-trifluoromethyloxiranyl)methyl]amino}-7-fluoro-1H-quinolin-2-oneHCID 46222190—
SolventDimethyl SulfoxideHCID 679—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product5-{[1-(2-Chloro-3-fluoro-4-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-(hydroxymethyl)propyl]amino}-7-fluoro-1H-quinolin-2-oneHCID 42623263379%

Reaction Steps

250 mg (0.54 mmol) 5-{[(2-chloro-3-fluoro-4-methoxyphenyl)(2-trifluoromethyl-oxiranyl)methyl]amino}-7-fluoro-1H-quinolin-2-on are stirred with 353 mg (1.1 mmol) Caesium carbonate in 3 ml DMF, 1.9 ml water and 0.5 ml DMSO. Water is added and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with brine and dried over sodium sulphate. After removal of the solvent flash chromatography on silica gel (methanol in dichloromethan 0 to 5%) yields 0.98 g of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08680117B2
Source datasetuspto-grants-2014_03
ORD IDord-edbe7b60527742ab8bb0b26601ab31c3
Source noteuspto-grants-2014_03