反应详情

温度

120 °C

To 3-bromo-1-(4-(trifluoromethyl)phenyl)-1H-1,2,4-triazole (5.64 g, 18.35 mmol) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (7.42 g, 33.9 mmol), tetrakis(triphenylphosphine) palladium(0) (3.30 g, 2.86 mmol), and potassium carbonate (7.82 g, 56.6 mmol) in 1,2-dimethoxyethane (75 mL) and water (18 mL). The mixture was degassed with nitrogen for 10 minutes. The reaction mixture was heated at 120° C. for 20 h. The reaction was cooled to room temperature and diluted with ethyl acetate (100 mL). The resultant salts were filtered and the filtrated layers were separated. The aqueous layer was separated with ethyl acetate (2×25 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated onto Celite®. Purification by silica gel chromatography using 0-100% ethyl acetate/hexanes as eluent provided the title compound as a yellow solid (4.16 g, 68%): 1H NMR (400 MHz, CDCl3) δ 8.60 (s, 1H), 8.03-7.97 (m, 2H), 7.88 (d, J=8.4 Hz, 2H), 7.77 (d, J=8.5 Hz, 2H), 6.79-6.74 (m, 2H), 3.88 (s, 2H); 13C NMR (101 MHz, CDCl3) δ 163.94, 148.07, 139.68, 129.67, 129.34, 128.04, 127.07, 127.04, 127.00, 126.96, 125.05, 120.50, 119.35, 114.87; 19F NMR (376 MHz, CDCl3) δ −62.43; ESIMS m/z 305.1 ([M+H]+).

1. customThe mixture was degassed with nitrogen for 10 minutes
2. temperatureThe reaction was cooled to room temperature
3. additiondiluted with ethyl acetate (100 mL)
4. filtrationThe resultant salts were filtered
5. customthe filtrated layers were separated
6. customThe aqueous layer was separated with ethyl acetate (2×25 mL)
7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
8. concentrationconcentrated onto Celite®
9. customPurification by silica gel chromatography