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【结 构 式】 
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【分子编号】22325 【品名】ethyl 2-[5-bromo-2-[(2,6-difluorobenzyl)oxy]phenyl]acetate 【CA登记号】 |
【 分 子 式 】C17H15BrF2O3 【 分 子 量 】385.2051064 【元素组成】C 53.01% H 3.92% Br 20.74% F 9.86% O 12.46% |
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：(IV)Simultaneous bromination and esterification of 2'-hydroxyphenylacetic acid (I) using tetrabutylammonium tribromide in EtOH at r.t. afforded (II), which was O-alkylated with alpha-bromo-2,6-difluorotoluene (III) in the presence of K2CO3 in refluxing acetone to yield ether (IV). Subsequent Heck olefination of (IV) with diethyl crotonamide (V) in the presence of palladium acetate and tri-o-tolylphosphine provided cinnamide (VI). The target carboxylic acid was then obtained by saponification of the ethyl ester of (VI) with NaOH.
| 【1】 Greenspan, P.D.; Fujimoto, R.A.; Marshall, P.J.; Raychaudhuri, A.; Lipson, K.E.; Zhou, H.; Doti, R.A.; Coppa, D.E.; Zhu, L.; Pelletier, R.; Uziel-Fusi, S.; Jackson, R.H.; Chin, M.H.; Kotyuk, B.L.; Fitt, J.J.; Carboxy-substituted cinnamides: A novel series of potent, orally active LTB4 receptor antagonists. J Med Chem 1999, 42, 1, 164. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 22322 | 2-(2-hydroxyphenyl)acetic acid | 614-75-5 | C8H8O3 | 详情 | 详情 |
| (II) | 22323 | ethyl 2-(5-bromo-2-hydroxyphenyl)acetate | C10H11BrO3 | 详情 | 详情 | |
| (III) | 22316 | 2-(bromomethyl)-1,3-difluorobenzene | 85118-00-9 | C7H5BrF2 | 详情 | 详情 |
| (IV) | 22325 | ethyl 2-[5-bromo-2-[(2,6-difluorobenzyl)oxy]phenyl]acetate | C17H15BrF2O3 | 详情 | 详情 | |
| (V) | 22326 | (E)-N,N-diethyl-2-butenamide | C8H15NO | 详情 | 详情 | |
| (VI) | 22327 | ethyl 2-[5-[(E)-3-(diethylamino)-1-methyl-3-oxo-1-propenyl]-2-[(2,6-difluorobenzyl)oxy]phenyl]acetate | C25H29F2NO4 | 详情 | 详情 |
Extended Information