反应详情

温度

120 °C

4-iodobenzotrifluoride (150 μL, 1 mmol), phenylpent-1-en-4-yn-3-ol (190 mg, 1.2 mmol), bis(triphenylphosphine)palladium(II) dichloride (14 mg, 0.02 mmol), copper iodide (3 mg, 0.03 mmol) and triphenylphosphine (52 mg, 0.2 mmol) were introduced in a 10 mL microwave vial flushed with argon. This was diluted with anhydrous triethylamine (700 μL, 4 mmol) in anhydrous degased 1,4-dioxane (1.3 mL). The solution was heated under microwave irradiation at 120° C. for 45 min. The reaction mixture was poured into a mix of 1M aqueous solution of hydrochloric acid (10 mL) and saturated aqueous ammonium chloride solution (10 mL), and this was extracted with dichloromethane (3×15 mL). The combined organic layers were dried over magnesium sulfate, filtered, and evaporated to dryness to give crude product which was purified by flash chromatography (SiO2, DCM/Hexanes 3:7). The resulting yellow solid was recrystallized (EtOH/Hexanes 1:3) to give pure final compound TG008A86 as a pale yellow powder (155 mg, 51%).

1. customvial flushed with argon
2. customin anhydrous degased 1,4-dioxane (1.3 mL)
3. additionThe reaction mixture was poured into
4. additiona mix of 1M aqueous solution of hydrochloric acid (10 mL) and saturated aqueous ammonium chloride solution (10 mL)
5. extractionthis was extracted with dichloromethane (3×15 mL)
6. dry with materialThe combined organic layers were dried over magnesium sulfate
7. filtrationfiltered
8. customevaporated to dryness
9. customto give crude product which
10. customwas purified by flash chromatography (SiO2, DCM/Hexanes 3:7)
11. customThe resulting yellow solid was recrystallized (EtOH/Hexanes 1:3)