945244-29-1, name is 5-Bromo-2-fluoro-4-methylaniline, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 945244-29-1
Method B: To 4 necked round bottom flask, equipped with mechanical agitation, thermometer, and N2 inlet is added 5-bromo-2-fiuoro-4-methylaniline (200g, 0.98 mol), CH3COOK (192g, 1.95 mol, 2.0eq), bis(pinacolato)diboron (248g, 0.98 mol,1.0eq) and IPAC (3L). After degassing with N2 for 30 min, the mixture is warmed to 50C and Pd(dppf)Cl2 (8g, 4wt%) is added. The reaction mixture is heated under reflux for at least lOh until the content of starting material <2% (GC). The mixture is cooled to 20~30C, filtered through a pad of Celite and rinsed with IPAC (1L). The filtrate is concentrated to 400~500ml remaining. The residue is mixed with n-Heptane (700ml), filtered through a Si02 pad and eluted with IPAC/n-Heptane(l/5 first, ~2L, and then 2/5, ~3L ). The filtrate is concentrated to 350~400ml. n-Heptane (300ml) is added and the mixture is again concentrated to 350~400ml. The residue (suspension) is cooled to -10- -20C and filtered after stirring for 2- 5 h. The crude product is dissolved in MeOH (200 ml) at 30-40 C, then slowly add H20 (600 ml) dropwise in 0.5~lh. The suspension is cooled to 20-30 C and filtered after stirring for 1-2 h .The solid is dried under high vacuum to afford the title compound as off- white solid (183g, 74% yield and 99% purity detected by UV absorption at 210 nm; 1H NMR (400 MHz, CDC13): delta 7.42 (d, J = 10.2 Hz, 1H), 7.01 (d, J = 12.4 Hz, 1H), 3.76 (s, 2H), 2.64 (s, 3H), 1.55 (s, 12H); 13C NMR(500MHz,CDC13): delta 20.66, 20.67, 24.40, 82.93, 116.20, 124.37, 130.64, 135.02, (151.93, 153.37);19F NMR (400 MHz,CDC13): delta 145.72
The synthetic route of 945244-29-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ELI LILLY AND COMPANY; DECIPHERA PHARMACEUTICALS, LLC; ALLGEIER, Matthew Carl; FLYNN, Daniel L.; KAUFMAN, Michael D.; PATEL, Phenil J.; WOLFANGEL, Craig D.; WO2013/134243; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary