With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.116131-44-3,3-(Bromomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.
To a solution of product of Example 1H (120 mg, 0.298 mmol) in N,N- dimethylformamide (2 mL) was added 3-(bromomethyl)tetrahydro-2//-pyran (117 mg, 0.656 mmol) and cesium carbonate (214 mg, 0.656 mmol). The reaction was heated to 80 C for 3 hours. The reaction was then cooled down to ambient temperature and partitioned between water (5 mL) and ethyl acetate (5 mL). The aqueous layer was further extracted with ethyl acetate (2 x 3 mL). The combined organic layers were washed with saturated aqueous ammonium chloride (5 mL) and dried over sodium sulfate. The volatiles were removed under reduced pressure, and the residue was subjected to column chromatography (Si(, 10% methanol in dichloromethane) to give afford the title compound (89 mg, 0.178 mmol, 60% yield). (501 MHz, DMSO-<) d ppm 7.75 (dd, / = 8.9, 1.4 Hz, 1H), 7.59 - 7.53 (m, 2H), 7.39 - 7.34 (m, 2H), 7.33 - 7.29 (m, 2H), 7.25 - 7.18 (m, 3H), 5.22 (s, 2H), 4.09 (s, 2H), 3.98 (dd, / = 6.6, 3.8 Hz, 2H), 3.95 - 3.90 (m, 1H), 3.34 - 3.28 (m, 2H), 3.79 - 3.72 (m, 1H), 3.31 (dd, / = 11.1, 9.1Hz, 1H), 2.09 - 2.01 (m, 1H), 1.89 (dd, / = 12.9, 4.3 Hz, 1H), 1.63 (dt, / = 13.0, 3.9 Hz, 1H), 1.59 - 1.48 (m, 1H), 1.48 - 1.38 (m, 1H); MS (APCT) mlz 499 [M-H]. 116131-44-3, The synthetic route of 116131-44-3 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; FARNEY, Elliot; SHIROODI, Roohollah, Kazem; XIONG, Zhaoming; ZHANG, Qingwei, I.; O’CONNOR, Matthew; HALVORSEN, Geoff; ZHAO, Hongyu; BAUMGARTNER, Christina; FROST, Jennifer, M.; KYM, Phil; ABBOTT, Jason, R.; BOGDAN, Andrew; ECONOMOU, Christos; WANG, Xueqing; (375 pag.)WO2019/246513; (2019); A1;,
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