Synthetic Route of 916766-83-1, A common heterocyclic compound, 916766-83-1, name is 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole, molecular formula is C11H11ClN2, 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.
To a mixture of 3- ( (3S, 4S) -4-hydroxytetrahydro-2H-pyran-3-yl) -7, 8-dimethyl-6- (4,4,5, 5-tetramethyl-l, 3, 2-dioxaborolan-2- yl) -2H-benzo [e] [1, 3] oxazin-4 (3H) -one (0.06 g), 3-(4- (chloromethyl) phenyl) -1-methyl-lH-pyrazole (0.03 g) and 2 M aqueous sodium carbonate solution (0.16 mL) in DME (3 mL) -water (0.3 mL) was added 1, 1′ -bis (diphenylphosphino) ferrocenepalladium (II) chloride (0.01 g) , and the mixture was subjected to microwave irradiation at 110C for 50 min. The. reaction mixture was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue waspurified by NH silica gel column chromatography (ethylacetate/hexane) and solidified with ethanol to give the title compound (0.02 g) .XH NMR (300 MHz, DMSO-d6) delta 1.39-1.60 (1H, m) , 1.83-1.97 (1H, m) , 2.11 (3H, s), 2.16 (3H, s) , 3.33-3.54 (2H, m) , 3.64-3.74 (1H, m) , 3.86 (6H, s) , 4.00 (2H, s) , 5.06 (1H, d, J = 5.3 Hz) , 5.20-5.40 (2H, m) , 6.61 (1H, d, J = 2.1 Hz), 7.12 (2H, d, J = 8.3 Hz), 7.46 (1H, s) , 7.63-7.73 (3H, m) .
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; SUGIMOTO, Takahiro; SUZUKI, Shinkichi; SAKAMOTO, Hiroki; YAMADA, Masami; NAKAMURA, Minoru; KAMATA, Makoto; SHIMOKAWA, Kenichiro; OGINO, Masaki; KIMURA, Eiji; MURAKAMI, Masataka; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); A1;,
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