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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 853484Generated: October 30, 2026

Dimethylformamide → tert-Butyl 4-(((4-(4-amino-3-fluorophenoxy)-6-cyano-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate

https://huagongshe.com/reaction/853484

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
Reactanttert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 15512811—
Reactant4-(4-Amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinolineHCID 135829379—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Producttert-Butyl 4-(((4-(4-amino-3-fluorophenoxy)-6-cyano-7-quinolyl)oxy)methyl)-1-piperidinecarboxylateHCID 2293677747.7%

Reaction Conditions

Temperature50 °C

Reaction Steps

After adding dimethylformamide (4 ml), tert-butyl 4-(bromomethyl)-1-piperidine carboxylate (708 mg) and potassium carbonate (467 mg) to 4-(4-amino-3-fluorophenoxy)-6-cyano-7-hydroxyquinoline (500 mg), the mixture was heated at 50° C. for 4 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate and the organic layer was washed with water and saturated brine in that order and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography (n-hexane:ethyl acetate) to obtain the title compound (398 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07253286B2
Source datasetuspto-grants-2007_08
ORD IDord-2f07b98fe636420bab033f2de7e77271
Source noteuspto-grants-2007_08