Synthetic Route of 153747-97-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.
Triflurooacetaldehyde hydrate (1.7 g, 14.6 mmol) was added dropwise into a stirred mixture consisting of phosphorus pentoxide (I g, 7.3 mmol) and 4 mL of concentrated sulfuric acid at 95 0C. The freshly produced gaseous trifluororacetaldehyde was trapped with a dry ice-filled cold finger and dripped into a THF solution of tert-butyl 4-(5- bromopyridin-2-yl)piperazine-l-carboxylate (I g, 2.92 mmol) with 2.5 M n-butyllithium in hexanes (1.3 mL, 3.2 mmol) at -78 0C under nitrogen atmosphere. After addition, the reaction mixture was warmed to room temperature and stirred for 2 h. The mixture was quenched with saturated ammonium chloride aqueous solution at -78 0C and the mixture was partitioned between DCM and brine. The organic layer was dried over Na2SO4 and concentrated to afford a brown solid. The crude material was purified by flash chromatography on silica gel, eluting with 10 – 80% EtOAc: heptane. Fractions containing the desired product were combined and concentrated to afford yellow sticky solid (450 mg, 42.6% yield). The Boc protected titled compound (380 mg, 1.1 mmol) was stirred in 20% TFA in DCM (5 mL) for 10 min. The reaction mixture was concentrated to afford the titled product as a TFA salt (260 mg, yield 95%). MS (m/z, MH+): meas. 262.2 calc. 262.25
The chemical industry reduces the impact on the environment during synthesis 153747-97-8, I believe this compound will play a more active role in future production and life.
Reference:
Patent; NOVARTIS AG; WO2008/110611; (2008); A1;,
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