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【结 构 式】 
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【分子编号】25750 【品名】2-methyl-5-(trimethylstannyl)pyridine 【CA登记号】 |
【 分 子 式 】C9H15NSn 【 分 子 量 】255.93484 【元素组成】C 42.24% H 5.91% N 5.47% Sn 46.38% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XIII)Finally, compound (VIII) is condensed with either trimethyl(6-methyl-3-pyridyl)tin (XIII) or the boronate ester lithium salt (XIV) by means of Pd(PPh3)4 to afford etoricoxib. The metalated pyridine (XIII) is obtained by esterification of 3-hydroxy-6-methylpyridine (XV) with triflic anhydride to give the corresponding triflate (XVI), which is treated with hexamethylditin to afford the target tin intermediate (XIII). The boronate lithium salt (XIV) is prepared by treatment of 5-bromo-2-methylpyridine (XVII) with n-BuLi followed by addition of triisopropyl borate.
| 【1】 Castañer, R.M.; Silvestre, J.S.; Sorbera, L.A.; Castañer, J.; Etoricoxib. Drugs Fut 2001, 26, 4, 346. |
| 【2】 Friesen, R.W.; Brideau, C.; Chan, C.C.; Charleson, S.; Deschenes, D.; Dube, D.; Ethier, D.; Fortin, R.; Gauthier, J.Y.; Girard, Y.; Gordon, R.; Greig, G.M.; Riendeau, D.; Savoie, C.; Wang, Z.; Wong, E.; Visco, D.; Xu, L.J.; Young, R.N.; 2-Pyridinyl-3-(4-methylsulfonyl)phenylpyridines: Selective and orally active cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett 1998, 8, 19, 2777. |
| 【3】 Dube, D.; Fortin, R.; Friesen, R.; Wang, Z.; Gauthier, J.Y. (Merck Frosst Canada Inc.); Substd. pyridines as selective cyclooxygenase-2 inhibitors. EP 0912518; JP 1999514008; US 5861419; WO 9803484 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 18565 | 2,5-dichloro-3-[4-(methylsulfonyl)phenyl]pyridine; 4-(2,5-dichloro-3-pyridinyl)phenyl methyl sulfone | C12H9Cl2NO2S | 详情 | 详情 | |
| (XIII) | 25750 | 2-methyl-5-(trimethylstannyl)pyridine | C9H15NSn | 详情 | 详情 | |
| (XIV) | 45704 | Lauroyl chloride | 112-16-3 | C15H27BLiNO3 | 详情 | 详情 |
| (XV) | 25748 | 6-methyl-3-pyridinol; 5-Hydroxy-2-methylpyridine | 1121-78-4 | C6H7NO | 详情 | 详情 |
| (XVI) | 25749 | 6-methyl-3-pyridinyl trifluoromethanesulfonate | C7H6F3NO3S | 详情 | 详情 | |
| (XVII) | 18566 | 5-bromo-2-methylpyridine | 3430-13-5 | C6H6BrN | 详情 | 详情 |
Extended Information