Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 432022-88-3, name is Methyl 4-bromo-3,5-dimethylbenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 432022-88-3
II?TERMEDIATE 49 Methyl 4- 5- 14-( (4S,5R)-5 – 13 -fluoro-5-(trifluoromethyl)phenyl] -4-methyl-2-oxo- 1,3 – oxazolidin-3-yBmethyl-2-(methylsulfanylnyrimidin-5-yl1-6-methoxynyridin-3-yB -3.5- dimethylbenzoateA mixture of (4S,5R)-3 – { [5-(5-chloro-2-methoxypyridin-3 -yl)-2-(methylsulfanyl)pyrimidin-4- yl]methyl} -5- [3 -fluoro-5-(trifluoromethyl)phenyl] -4-methyl- 1,3 -oxazolidin-2-one(INTERMEDIATE 18, 211 mg, 0.389 mmol), bis(pinacolato)diboron (296 mg, 1.17 mmol), and potassium acetate (114 mg, 1.17 mmol) in N,N-dimethylacetamide (2.0 mL) was degassed three times with nitrogen gas before the addition of(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl) [2-(2-aminoethyl)phenyl)]palladium(II) chloride (XPHOS Biphenyl Precatalyst) (15.5 mg, 0.0 19 mmol). The system was degassed three times and was then heated to 130 C for24 hours. LC/MS analysis indicated complete conversion to the product, but almost exclusively as the boronic acid. For this reason the crude reaction mixture was taken directly into the next step. Accordingly, methyl 4-bromo-3 ,5-dimethylbenzoate (142 mg, 0.584 mmol), (1,1 bis(di tert-butylphosphino)ferrocene palladium dichloride (24.5 mg, 0.039 mmol), and aqueous potassium carbonate (0.389 mL, 2.0 M) were added. The mixture was degassed, flushed withnitrogen and heated to 100C for 45 minutes. The reaction was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography to afford methyl 4-{5-[4-({(4S,5R)-5-[3-fluoro- 5-(trifluoromethyl)phenyl] -4-methyl-2-oxo- 1,3 -oxazolidin-3-yl} methyl)-2- (methylsulfanyl)pyrimidin-5-yl] -6-methoxypyridin-3 -yl} -3 ,5-dimethylbenzoate (158 mg, 0.236mmol). LCMS (M+H)*: 671.1
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; MERCK SHARP & DOHME CORP.; ACTON, John, J., III; YE, Feng; VACHAL, Petr; SHA, Deyou; DROPINSKI, James, F.; CHU, Lin; ONDEYKA, Debra; KIM, Alexander, J.; COLANDREA, Vincent, J.; ZANG, Yi; ZHANG, Fengqi; DONG, Guizhen; WO2013/165854; (2013); A1;,
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