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【结 构 式】

【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%

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:(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
Extended Information