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【结 构 式】

【分子编号】55081

【品名】2-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-fluorophenyl)-2-(4-pyridinyl)-1-ethanol

【CA登记号】

【 分 子 式 】C19H26FNO2Si

【 分 子 量 】347.5048832

【元素组成】C 65.67% H 7.54% F 5.47% N 4.03% O 9.21% Si 8.08%

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)

4-[(tert-Butyldimethylsilyloxy)methyl]pyridine (II) was prepared by silylation of 4-hydroxymethylpyridine (I) with tert-butyldimethylsilyl chloride and imidazole. Deprotonation of (II) by means of LDA in cold THF, followed by condensation with 4-fluorobenzaldehyde (III), furnished the protected diol adduct (IV), which was further desilylated upon treatment with tetrabutylammonium fluoride in THF. Oxidation of the resultant diol (V) under Swern conditions provided diketone (VI). The triaryl imidazole (VIII) was then obtained by condensation of diketone (VI) with 4-(methylsulfanyl)benzaldehyde (VII) in the presence of ammonium acetate in refluxing HOAc. Finally, oxidation of the thioether function of (VIII) with K-2S2O8 furnished the title sulfoxide.

1 Adams, J.L.; Gallagher, T.F.; Lee, J.C.; White, J.R. (GlaxoSmithKline plc); Imidazole derivs. and their use as cytokine inhibitors. EP 0623126; EP 0943616; JP 1995503017; US 5686455; WO 9314081 .
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) 32835 4-pyridinylmethanol 586-95-8 C6H7NO 详情 详情
(II) 22829 4-([[tert-butyl(dimethyl)silyl]oxy]methyl)pyridine; tert-butyl(dimethyl)silyl 4-pyridinylmethyl ether C12H21NOSi 详情 详情
(III) 12337 4-fluorobenzaldehyde 459-57-4 C7H5FO 详情 详情
(IV) 55081 2-{[tert-butyl(dimethyl)silyl]oxy}-1-(4-fluorophenyl)-2-(4-pyridinyl)-1-ethanol C19H26FNO2Si 详情 详情
(V) 55082 1-(4-fluorophenyl)-2-(4-pyridinyl)-1,2-ethanediol C13H12FNO2 详情 详情
(VI) 37913 1-(4-fluorophenyl)-2-(4-pyridinyl)-1,2-ethanedione C13H8FNO2 详情 详情
(VII) 18815 4-(methylsulfanyl)benzaldehyde; 4-(methylmercapto)benzaldehyde 3446-89-7 C8H8OS 详情 详情
(VIII) 55083 4-{5-(4-fluorophenyl)-2-[4-(methylsulfanyl)phenyl]-1H-imidazol-4-yl}pyridine; 4-[5-(4-fluorophenyl)-4-(4-pyridinyl)-1H-imidazol-2-yl]phenyl methyl sulfide C21H16FN3S 详情 详情
Extended Information