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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1010435Generated: October 30, 2026

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

https://huagongshe.com/reaction/1010435

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—
SolventHexaneHCID 8058—
SolventEthyl AcetateHCID 8857—
Producttert-Butyl 4-(((4-(4-amino-3-fluorophenoxy)-6-cyano-7-quinolyl)oxy)methyl)-1-piperidinecarboxylateHCID 2293677750.7%

Reaction Steps

4-(4-Amino-3-fluorophenoxy)-7-hydroxy-6-quinoline carbonitrile (500 mg), tert-butyl 4-(bromomethyl)-1-piperidinecarboxylate (550 mg), potassium carbonate (700 mg) and dimethylformamide (5 ml) were stirred together at 60° c. for 2 hours. Water and ethyl acetate were added for extraction, and the extract was dried over magnesium sulfate. The drying agent was filtered out, and silica gel was added to the filtrate which was then distilled off under reduced pressure for adsorption. The reaction solution-adsorbed silica gel was subjected to column chromatography (hexane:ethyl acetate=1:1, followed by 1:2, 1:3, ethyl acetate) in a dry column packed with silica gel, to obtain 423 mg of a brown oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07973160B2
Source datasetuspto-grants-2011_07
ORD IDord-16e1e708bd0c49e6b796c05fc59428b0
Source noteuspto-grants-2011_07