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【结 构 式】 
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【分子编号】37876 【品名】methyl 2-hydroxy-5-[2-(trimethylsilyl)ethynyl]benzoate 【CA登记号】 |
【 分 子 式 】C13H16O3Si 【 分 子 量 】248.35374 【元素组成】C 62.87% H 6.49% O 19.33% Si 11.31% |
合成路线1
该中间体在本合成路线中的序号：(III)Palladium-catalyzed coupling of methyl 5-iodosalycilate (I) with trimethylsilyl acetylene (II) produced the ethynyl salycilate (III). The trimethylsilyl protecting group of (III) was then cleaved by treatment with KF in DMF to give (IV). On the other hand, sulfonamide (VII) was obtained by condensation of 4-iodobenzenesulfonyl chloride (V) with 2-amino-3-methylpyridine (VI). A further Suzuki coupling between acetylene (IV) and iodosulfonamide (VII) furnished diaryl acetylene (VIII). The methyl ester group of (VIII) was finally saponified with NaOH to provide the target carboxylic acid.
| 【1】 Agback, H.; Ahrgren, L.; Berglindh, T.; Haraldsson, M.; Smedegard, G.; Olsson, L.-I. (Pharmacia & Upjohn AB); Substd. salicylic acids. JP 1995501330; US 5403930; WO 9310094 . |
| 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) | 37875 | methyl 2-hydroxy-5-iodobenzoate | C8H7IO3 | 详情 | 详情 | |
| (II) | 23897 | ethynyl(trimethyl)silane；trimethylsilyl acetylene | 1066-54-2 | C5H10Si | 详情 | 详情 |
| (III) | 37876 | methyl 2-hydroxy-5-[2-(trimethylsilyl)ethynyl]benzoate | C13H16O3Si | 详情 | 详情 | |
| (IV) | 37877 | methyl 5-ethynyl-2-hydroxybenzoate | C10H8O3 | 详情 | 详情 | |
| (V) | 27811 | 4-iodobenzenesulfonyl chloride | 98-61-3 | C6H4ClIO2S | 详情 | 详情 |
| (VI) | 13016 | 3-Methyl-2-pyridinylamine; 3-Methyl-2-pyridinamine; 2-Amino-3-picoline; 2-Amino-3-methylpyridine | 1603-40-3 | C6H8N2 | 详情 | 详情 |
| (VII) | 37878 | 4-iodo-N-(3-methyl-2-pyridinyl)benzenesulfonamide | C12H11IN2O2S | 详情 | 详情 | |
| (VIII) | 37879 | methyl 2-hydroxy-5-[2-(4-[[(3-methyl-2-pyridinyl)amino]sulfonyl]phenyl)ethynyl]benzoate | C22H18N2O5S | 详情 | 详情 |