With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.
KHMDS (1M in THF) (39.0 mL, 39.0 mmol) was added to THF (150 mL) at -78C under nitrogen. A solution of 1-(tetrahydro-2H-pyran-4-yl)ethanone (5 g, 39.0 mmol) in THF (20 mL) was added and the mixture was stirred at -78C under nitrogen for 1 .5h, giving a pale yellow solution. A solution of N-(5- chloropyridin-2-yl)-1 ,1 ,1 -trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide (15.32 g, 39.0 mmol) in THF (25 mL) was added over 20 minutes and the resulting orange, then colourless mixture was allowed to warm slowly to room temperature and stirred overnight. The reaction was quenched with NaHCO3 and the crude product extracted with MTBE (300 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under vacuum. The residue was dissolved in a small amount of 10% EtOAc:lsohexane and loaded on a 40g column. The crude product was purified by chromatography (Si02, 40 g column, 0-10% EtOAc/isohexane). Fractions containing product were combined, filtered, washing with 10% EtOAc:lsohexane, then concentrated. A solid formed in the residue, which was then taken up in 10% EtOAc:lsohexane, filtered through cotton wool. The filtrate was then loaded on a 40g column and the crude product was purified by chromatography (Si02, 40 g column, 0-10% EtOAc/isohexane) to afford 1 -(tetrahydro-2H-pyran-4-yl)vinyl trifluoromethanesu Ifonate (6.17 g, 20.15 mmol, 51.7% yield) as a colourless oil. 1H NMR (CDCI3) O: 5.14 (dd, 1H), 4.94 (dd, 1H), 4.06 – 3.98 (m, 2H), 3.41 (td, 2H), 2.54 -2.41 (m, 1 H), 1.89 – 1.79 (m, 2H), 1.66 – 1.50 (m, 2H)., 137052-08-5
The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; HOWARD, Steven; CONS, Benjamin, David; ST. DENIS, Jeffrey, David; GRIFFITHS-JONES, Charlotte, Mary; HISCOCK, Steven, Douglas; HOLVEY, Rhian, Sara; BURNS, Alan, Richard; COUSIN, David; DEXTER, Hannah, Louise; PARRA, Guillaume, Francois; WATTS, John, Paul; JEWELL, Robert; STOCKWELL, Jennifer, Ann; HIRST, Kim, Louise; LEMASSON, Isabelle, Anne; NASH, David, John; OSBORNE, James, Daniel; PRIEDE, Jonas, Calleja; RICHARDS, Nicholas, Paul; DUMAS, Aaron, Michael; BISHOP, Brian, Christopher; PARRY-JONES, David; SCOTT, Jeremy, Peter; SHAUNMUGHAM, Meenakshi, Sundaram; MULLENS, Peter, Richard; LATHBURY, David, Charles; DIXON, Darren, James; GAUNT, Matthew, James; (291 pag.)WO2018/178691; (2018); A1;,
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