Sodium Iodide → HCID 89586480, compound

Participants

Reaction Steps

Sodium iodide (0.2772 g) and chlorotrimethylsilane (0.235 mL) were stirred in acetonitrile (1.85 mL) at room temperature for 30 min. A solution of 5-methoxy-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.100 g) in acetonitrile (3.7 mL) was added at room temperature. The reaction mixture was heated under reflux for 3 hr. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated, purified by silica gel column chromatography (ethyl acetate/hexane-methanol/ethyl acetate), and concentrated under reduced pressure. The obtained residue, potassium carbonate (0.1125 g) and 2-(chloromethyl)quinoline hydrochloride (0.0871 g) were suspended in N,N-dimethylformamide (2 mL), and the mixture was stirred at room temperature for 14 hr, and at 60° C. for 5 hr. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane), silica gel column chromatography (ethyl acetate/hexane) and HPLC, and recrystallized from ethyl acetate/hexane to give the title compound (0.0527 g).

Provenance & Evidence