With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.
To tert-butyl 3-(5-chloro-2-fluoropyridin-4-yl)phenylcarbamate (270 mg, 0.837 mmol) in DMF (3 rriL) was added slowly sodium hydride (60 wt.% in mineral oil, 40.1 mg) at 0 C. The ice bath was removed and the crude mixture was stirred for 20 min at room temperature. To the crude mixture was added (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (271 mg, 1.004 mmol) and stirring was continued at 40 C for 40 hrs. The reaction mixture was cooled to room temperature and diluted with EtOAc (150 mL). The mixture was washed saturated aqueous sodium bicarbonate solution (2x), water (2x) and brine (lx), dried with sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 24 g, EtO Ac/heptane = 0/100 to 30/70] providing [3-(5-chloro-2- fluoro-pyridin-4-yl)-phenyl]-(tetrahydro-pyran-4-ylmethyl)-carbamic acid tert-butyl ester (205 mg). LCMS (m/z): 421.2 [M+H]+; Retention time = 1.19 min.
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Reference£º
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; MARTIN, Eric J.; PAN, Yue; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/66065; (2012); A1;,
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