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In a dry reaction tube containing in suspension copper iodide (28 mg, 0.148 mol) and triethylamine (8.30 mL, 59.20 mmol), were added 3-fluoro-2-iodopyridine (660 mg, 2.96 mmol) and Pd(PPh3)2Cl2 (104 mg, 0.148 mmol) under N2. A yellow suspension was obtained. After a 5 minutes of stirring at room temperature, was added a solution 2-(But-3-ynyl)benzo[d]oxazole (compound 8(A), 510 mg, 3 mmol) in triethylamine (0.2 mL) under N2. Immediately the color of the reaction turns to black. The mixture was stirred at room temperature for 30 min and heated at 50° C. overnight under N2. Triethylamine was removed under reduce pressure and the crude product was purified by flash chromatography (Prepacked column 50 g, Cyclohexane/AcOEt: 60/40 as eluent) following by C18 chromatography (Prepacked column 15 g, H2O/CH3CN: from 80/20 to 40/600 as eluent) to afford 120 mg of 2-(4-(3-fluoropyridin-2-yl)but-3-ynyl)benzo[d]oxazole (Yield: 15%) as white powder (Mp=86-88° C.).

1. customIn a dry reaction tube
2. customA yellow suspension was obtained
3. stirringThe mixture was stirred at room temperature for 30 min
4. temperatureheated at 50° C. overnight under N2
5. customTriethylamine was removed
6. customthe crude product was purified by flash chromatography (Prepacked column 50 g, Cyclohexane/AcOEt: 60/40 as eluent)