4-Fluoroiodobenzene → 1-(4-fluorophenyl)-6-[3-(pyrrolidin-1-yl)propoxy]-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-[3-(pyrrolidin-1-yl)propoxy]-3,4-dihydroquinolin-2(1H)-one prepared in Example 10-(2) (0.20 g), 1-fluoro-4-iodobenzene (0.24 g), rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (0.10 g), copper iodide (0.035 g) and cesium carbonate (0.48 g) in toluene (1.0 mL) was stirred at 105° C. for 60 hours. The reaction mixture was cooled to room temperature, diluted with chloroform and filtered to remove insoluble materials. The filtrate was concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1), and the resulting solid was subjected to recrystallization from a mixture of diisopropyl ether and ethyl acetate to give the titled compound (0.10 g, 37%) as a colorless solid.

Provenance & Evidence