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【结 构 式】

【分子编号】22250

【品名】4-ethynylphenyl 3-(1H-imidazol-4-yl)propyl ether; 4-[3-(4-ethynylphenoxy)propyl]-1H-imidazole

【CA登记号】

【 分 子 式 】C14H14N2O

【 分 子 量 】226.27804

【元素组成】C 74.31% H 6.24% N 12.38% O 7.07%

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:(IX)

4-Iodophenol (I) was protected as the trimethylsilyl ether (II) with Me3SiCl and then coupled with (trimethylsilyl)acetylene (III) using palladium catalyst and CuI to afford the O-desilylated ethynylphenol (IV). This was condensed under Mitsunobu conditions with N-Boc-imidazolylpropanol (VI), prepared from imidazolylpropanol (V) and Boc2O, to afford ether (VII). Deprotection of the Boc group of (VII) with methanolic hydrazine at r.t. yielded a mixture of (VIII) and the fully desilylated analogue (IX), which was isolated by column chromatography and finally crystallized as the maleate salt from EtOH-Et2O.

1 Krause, M.; Ligneau, X.; Stark, H.; Garbarg, M.; Schwartz, J.C.; Schunack, W.; 4-Alkynylphenyl imidazolylpropyl ethers as selective histamine H3-receptor antagonists with high oral central nervous system activity. J Med Chem 1998, 41, 21, 4171.
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) 22242 4-iodophenol 540-38-5 C6H5IO 详情 详情
(II) 22243 (4-iodophenoxy)(trimethyl)silane; 4-iodophenyl trimethylsilyl ether C9H13IOSi 详情 详情
(III) 23897 ethynyl(trimethyl)silane;trimethylsilyl acetylene 1066-54-2 C5H10Si 详情 详情
(IV) 22245 4-[2-(trimethylsilyl)ethynyl]phenol C11H14OSi 详情 详情
(V) 21245 3-(1H-imidazol-4-yl)-1-propanol C6H10N2O 详情 详情
(VI) 22247 tert-butyl 4-(3-hydroxypropyl)-1H-imidazole-1-carboxylate C11H18N2O3 详情 详情
(VII) 22248 tert-butyl 4-(3-[4-[2-(trimethylsilyl)ethynyl]phenoxy]propyl)-1H-imidazole-1-carboxylate C22H30N2O3Si 详情 详情
(VIII) 22249 4-(3-[4-[2-(trimethylsilyl)ethynyl]phenoxy]propyl)-1H-imidazole; 3-(1H-imidazol-4-yl)propyl 4-[2-(trimethylsilyl)ethynyl]phenyl ether C17H22N2OSi 详情 详情
(IX) 22250 4-ethynylphenyl 3-(1H-imidazol-4-yl)propyl ether; 4-[3-(4-ethynylphenoxy)propyl]-1H-imidazole C14H14N2O 详情 详情
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