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.
To a solution of 7-(3-hydroxyphenyl)-5-methyl-2-((4-(methylsulphonyl)piperazin-1- yl)methyl)thieno[3,2-c]pyridin-4(5H)-one (for a preparation see Example 10, 17 mg, 0.039 mmol) and 4-(bromomethyl)tetrahydro-2H-pyran (21 .06 mg, 0.1 18 mmol) in A/,A/-dimethylformamide (2 mL) was added potassium carbonate (16.26 mg, 0.1 18 mmol). The resulting mixture was stirred at 100 C for 3 hours, whereupon it was allowed to cool to room temperature. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted 3 times with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 2-10% methanol in dichloromethane. The appropriate fractions were combined and concentrated in vacuo to give 5-methyl-2-((4-(methylsulphonyl)piperazin-1-yl)methyl)-7-(3- ((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)thieno[3,2-c]pyridin-4(5H)-on (13 mg, 0.025 mmol, 65%). LCMS (2 min, Formic Acid): Rt = 0.80 min, MH+ = 532
125552-89-8, 125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.
Reference£º
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; BAMBOROUGH, Paul; BIT, Rino, Antonio; BROWN, John, Alexander; CAMPBELL, Matthew; LINDON, Matthew, John; SHIPLEY, Tracy, Jane; THEODOULOU, Natalie, Hope; WELLAWAY, Christopher, Roland; WESTAWAY, Susan, Marie; WO2014/78257; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics