反应详情

温度

80 °C

To a stirred solution of 7-bromo-6-chloro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline (143-7; 0.20 g, 0.0006 mol) and (5-fluoropyridin-3-yl)boronic acid (0.93 g, 0.0006 mol) in the mixture of 1,4-dioxan (10 mL) and water (10 mL) was added sodium carbonate (0.127 g, 0.0012 mol). Reaction mass was purged with argon for 20 min. Then catalyst Pd(dppf)2Cl2 (0.048 g, 0.00006 mol) was added and allowed to stir at 80° C. for 12 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic part was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.659-8.652 (d, J=2.8 Hz, 1H), 8.514 (s, 1H), 7.908-7.884 (d, J=9.6 Hz, 1H), 7.789-7.768 (d, J=8.4 Hz, 1H), 7.566-7.504 (d, J 8.4 Hz, 1H), 3.186-3.152 (m, 2H), 3.084-3.035 (m, 2H), 2.695 (s, 3H). MS (M+1): 315.1.

1. customReaction mass
2. customwas purged with argon for 20 min
3. filtrationThe reaction mixture was filtered through CELITE bed
4. filtrationfilter bed
5. washwas thoroughly washed with ethyl acetate
6. concentrationThe collected organic part was concentrated under vacuum
7. customto afford the crude compound, which
8. customwas purified by silica gel column chromatography