36942-56-0, These common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, 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 solution of compound 1 (120 g, 0.59 mol, 1.0 equiv, F-chemicals), compound 2 (101.4 g, 0.65 mol, 1.1 equiv, combi blocks) and potassium carbonate (247.1 g, 1.79 mol, 3.0 equiv) in 1,4-dioxane (2.0 L) and H2O (500 mL) was degassed with N2 for 15 min. Pd(PPh3)4 (34.4 g, 0.029 mol, 0.05 equiv) was added and the mixture was again degassed with N2 gas for 5 min. The reaction mixture was heated at 90 C. for 3 h. The reaction mass was cooled to RT, diluted with ethyl acetate (2.0 L) and washed with brine (1.0 L). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to get the crude material which was purified by column chromatography (silica gel 60-120 mesh, elution 1% EtOAc/Hexane) to get the pure compound 3 (110 g, 79%). TLC solvent system: heptane, Product Rf: 0.5. 1H NMR (300 MHz, Chloroform-d) delta 7.40-7.29 (m, 3H), 7.26-7.14 (m, 2H), 6.85 (dd, J=8.4, 2.7 Hz, 1H), 6.77 (d, J=2.6 Hz, 1H), 3.81 (s, 3H), 2.19 (s, 3H).
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 36942-56-0.
Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
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