Methyl iodide → 4-Ethoxy-6-[2-methylsulfanyl-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-quinoline-3-carbonitrile

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To the suspension of 4-ethoxy-6-[4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile (example 14f) (1.7 g, 5 mmol), iodomethane (0.62 mL, 10 mmol) and DIEA (diisopropylethylamine) (1.7 mL, 10 mmol) in anhydrous ethanol (25 mL) was stirred at room temperature for 24 h. After adding hexane (50 mL), the solid was collected by filtration, washed with hexane and dried. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-5% methanol in methylene chloride in 30 min) afforded to obtain 4-ethoxy-6-[2-methylsulfanyl-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile(1.25 g, 75%) as a yellow solid. LC-MS m/e 356 (MH+)

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