As a common heterocyclic compound, it belongs to naphthyridine compound, name is 3-Bromo-1,5-naphthyridine, and cas is 17965-71-8, its synthesis route is as follows.,17965-71-8
General procedure: To a solution of aryl bromide (0.3mmol) in anhydrous 1,4-dioxane (10mL) was added boronic acid (0.45mmol) and a solution of K3PO4 (130mg, 0.61mmol) in water (2mL). The mixture was purged with nitrogen gas for 5min. Pd(dppf)Cl2.CH2Cl2 (12mg, 0.015mmol) was added and the mixture was heated at 100C. After 5h, the reaction mixture was cooled to room temperature, filtered through celite and washed with ethyl acetate. The filtrate was washed with water (50mL), brine (50mL), dried (anhydrous Na2SO4) and concentrated under reduced pressure. The residue was purified by preparative HPLC (C18 column, 20:80 acetonitrile/water with 0.1% formic acid). Compound containing fractions were lyophilized to afford the product. 5.1.2 1-(5-(1,5-Naphthyridin-3-yl)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-2-yl)-3-ethylurea (6) (0026) Synthesized from 4 and 5 following the general procedure for Suzuki coupling in 58% yield as a pale yellow solid. 1H NMR (400MHz, DMSO-d6) delta 9.52 (s, 1H), 9.05-9.04 (m, 1H), 8.82-8.81 (m, 1H), 8.50-8.46 (m, 4H), 8.26 (s, 1H), 7.85-7.82 (m, 1H), 7.62-7.59 (m, 1H), 3.27-3.19 (m, 2H), 1.12 (t, 3H, J=7.2Hz); 13C NMR (100MHz, DMSO-d6) delta 165.7, 153.7, 153.5, 151.6, 151.3, 149.1, 142.8, 142.4, 142.2, 142.0, 141.8, 138.7, 136.4, 136.1, 132.7, 125.7, 125.6, 124.5, 123.6, 120.9, 118.3, 115.6, 109.6, 33.4, 14.7. MS (ESI) m/z 445.1 (M+H)+; HRMS: calcd for C20H15F3N6OS (M+H)+, 445.1053; found, 445.1046. mp: 232.4-232.7C.
With the complex challenges of chemical substances, we look forward to future research findings about 3-Bromo-1,5-naphthyridine
Reference£º
Article; Ho, Soo Yei; Wang, Weiling; Ng, Fui Mee; Wong, Yun Xuan; Poh, Zhi Ying; Tan, Sum Wai Eldwin; Ang, Shi Hua; Liew, Si Si; Joyner Wong, Yin Sze; Tan, Yvonne; Poulsen, Anders; Pendharkar, Vishal; Sangthongpitag, Kanda; Manchester, John; Basarab, Gregory; Hill, Jeffrey; Keller, Thomas H.; Cherian, Joseph; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 610 – 621;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem