Cesium carbonate → 4-[6-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}-2-oxo-3,4-dihydroquinolin-1(2H)-yl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

A suspension of (2R)-6-[3-(2-methylpyrrolidin-1-yl)propoxy]-3,4-dihydroquinolin-2(1H)-one prepared in Example 1-(2) (0.20 g), 4-iodobenzonitrile (0.18 g), rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (0.041 g), copper iodide (0.013 g) and cesium carbonate (0.45 g) in N,N-dimethylformamide (2 mL) was stirred at 100° C. for 16 hours. The reaction mixture was diluted with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by preparative TLC (on a single plate of 2 mm thickness, developing solvent: chloroform/methanol=9/1) and NH-type preparative TLC (on two plates of 0.25 mm thickness, developing solvent: n-hexane/ethyl acetate=1/1) to give the titled compound (0.062 g, 23%) as a light-brown amorphous substance.

Provenance & Evidence