As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate
A mixture of 1-28 (4.30 g, 12.57 rnmol), bis(pinacolato)diboron (3.82 g, 15.07 mmcl) and KOAc (2.94 g, 37.69 mmcl) in 1,4-dioxane (30 mL) was degassed in a stream of argon for 15 minutes. To the mixture was added 1,1- bis (diphenylphosphino) ferrocenepalladium(II) dichloridedichloromethane complex (0.307 g, 0.376 mmcl), and the reaction mixture was again degassed for additional 15 minutes. After stirring at 100C for 20 hours, the volatiles were removed by evaporation, and the obtained residue was diluted with water (50 mL), followed by extraction with ethyl acetate(50 mL x 3) . The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (100-200 mesh) using 50% EtOAc in hexanes to give the desired product Intermediate 1-CII as a mixture of minor boronate ester together with major boronic acid (4.8 g, crude yield 98%) as a yellow solid; IJCMS (for boronate ester): m/z 390.2 [M+1]; LCMS (for boronic acid): m/z 308.1 [M+1].
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Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOUL, Summon; KURHADE, Suresh; NAIK, Keshav; SALUNKHE, Videsh; KULKARNI, Rakesh; PARDESHI, Vishwajeet; BHUNIYA, Debnath; KULKARNI, Bheemashankar; MOOKHTIAR, Kasim Abbaas; (274 pag.)WO2017/38909; (2017); A1;,
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