Application of 869557-43-7 ,Some common heterocyclic compound, 869557-43-7, molecular formula is C5H4BrFN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
A mixture of 10 g of 2-amino-3-bromo-5-fluoropyridine, 19.2 g of 5-chloro-4-(trimethylstannyl)-2,3′-bipyridine A1, 4.24 g of tetrakis(triphenylphosphine)-palladium(0) and 2.095 g of copper (I) iodide in 120 ml of 1,4-dioxane is refluxed for 18 hours. The reaction medium is treated with aqueous 10% sodium hydrogen carbonate solution and then diluted with ethyl acetate. After separation of the phases by settling, the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is taken up in a mixture of dichloromethane and methanol, and is then filtered by suction to give 11.67 g of 5′-chloro-5-fluoro-3,2′:4′,3-terpyridin-2-amine in the form of a beige-coloured solid. The filtrate is concentrated under reduced pressure and then taken up in dichloromethane, and silica is added. After concentrating under reduced pressure, the deposit is purified by chromatography on a column of silica, eluting with a 98/2 to 90/10 dichloromethane/methanol mixture to give 1.98 g of 5′-chloro-5-fluoro-3,2′:4′,3-terpyridin-2-amine in the form of a beige-coloured solid.UPLC-MS-DAD-ELSD: Tr (min)=2.71; [M+H]+: m/z 301; purity: 95%1H NMR (400 MHz, DMSO-d6): ppm: 5.78 (s, 2H) 7.47 (dd, J=8.8, 2.9 Hz, 1H) 7.55 (br. s., 1H) 8.06 (s, 1H) 8.12 (s, 1H) 8.49 (d, J=7.8 Hz, 1H) 8.68 (br, s., 1H) 8.84 (s, 1H) 9.35 (br. s., 1H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,869557-43-7, its application will become more common.
Reference:
Patent; SANOFI; US2012/208809; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem