With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.
V-tert-Butyl-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-({[2-(4-chloro-2-hydroxyphenyl) ethyl]sulfonyl}amino)benzenesulfonamide (4.05 g, 5.67 mmol) devided in three vials (1.35 g, 1.89 mmol in each vial), cesium carbonate (2.77 g, 8.49 mmol in each vial), 4- bromomethyltetrahydropyran (1.52 g, 8.49 mmol in each vial) and Lambda/,/V-dimethylformamide (12 mL in each vial) were mixed and heated in a MW at 110 C for 1 h. The reaction mixtures were filtered and the solvent was evaporated. The combined crude product was mixed with water/ethyl acetate and the aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and the solvent was evaporated. Purification by chromatography on silica using gradient elution 5- 50 % EtOAc in heptane gave 3.23 g (70 % yield) of the title compound. XH NMR (500 MHz, DMSO-de) delta ppm 1.04 (s, 9 H) 1.08 (s, 9 H) 1.11 (s, 1 H) 1.18 – 1.28 (m, 2 H) 1.52 – 1.58 (m, 2 H) 1.83 – 1.91 (m, 1 H) 2.94 – 2.99 (m, 2 H) 3.20 – 3.27 (m, 2 H) 3.44 – 3.49 (m, 2 H) 3.79 (m, 3 H) 4.79 (s, 2 H) 6.91 (dd, 1 H) 7.01 (d, 1 H) 7.18 (d, 1 H) 7.40 – 7.45 (m, 4 H) 7.46 (d, 2 H) 7.52 (dd, 1 H) 7.61 – 7.65 (m, 5 H) 7.99 (s, 1 H) 8.03 (d, 1 H) 8.73 (s, 1 H). MS (ES ) m/z 811,813 [M-H]”., 125552-89-8
The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; ACTURUM LIFE SCIENCE AB; SOeDERMAN, Peter; SVENSSON, Mats A; KERS, Annika; OeHBERG, Liselott; HOeGDIN, Katharina; HETTMAN, Andreas; HALLBERG, Jesper; EK, Maria; BYLUND, Johan; NORD, Johan; (0 pag.)WO2016/85392; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics