To a 100 mL 3 neck flask equipped with magnetic stirrer, addition funnel, and nitrogen inlet was charged 2.13 grams (g) of 6-(5-chloropyridin-2-yl)pyridazin-3(2H)-one (10.3 mmol), 2.20 g of potassium carbonate (16 mmol), and 50 mL of dry DMF. The reaction mixture was stirred for about 30 minutes at ambient temperature followed by the dropwise addition of 2.54 g of 4-(pentyloxy)but-2-ynyl methanesulfonate (10.8 mmol) in about 5 mL of dry DMF. The reaction was stirred overnight at ambient temperature, and checked by TLC and GC the next morning. No starting material remained, and one new product was formed. The reaction was poured into about 100 mL of water, and extracted with 3×50 mL of ethyl ether. The combined ether extract was washed with 100 mL of water, 100 mL of saturated aqueous sodium chloride solution, dried, and stripped to the crude product which was purified by silica gel column chromatography. The pure fractions were combined and concentrated under vacuum on a rotary evaporator to afford 1.3 g of a white solid. The NMR data is as follows: 300 MHz 1H NMR (CDCl3, TMS=0 ppm) 0.90 (m 3H); 1.30 (m, 4H); 1.55 (m, 2H); 3.45 (t, 2H); 4.15 (s, 2H); 5.05 (s, 2H); 7.05 (d, 1H); 7.75 (d, 1H); 8.15 (d, 1H); 8.30 (d, 1H); 8.55 (s, 1H).
