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【结 构 式】

【分子编号】61341

【品名】6-(3-(1-adamantyl)-4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)nicotinaldehyde

【CA登记号】

【 分 子 式 】C28H37NO2Si

【 分 子 量 】447.69282

【元素组成】C 75.12% H 8.33% N 3.13% O 7.15% Si 6.27%

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:(VII)

Coupling between 4-bromophenol (I) and 1-adamantanol (II) in the presence of H2SO4 affords the adamantanyl phenol (III), which is further protected as the silyl ether (IV) by means of t-butyldimethylsilyl chloride and DMAP. Addition of triisopropyl borate to the organolithium derivative of (IV) gives rise, after aqueous quenching, to the boronic acid (V). Then, Suzuki coupling of boronic acid (V) with 6-bromopyridine-3-carbaldehyde (VI) furnishes the phenylpyridine adduct (VII). Desilylation of (VII) to provide phenol (VIII) is accomplished by treatment with tetrabutylammonium fluoride in THF. Finally, condensation of pyridine aldehyde (VIII) with 2,4-thiazolidinedione (IX) under Knoevenagel conditions provides the target compound

1 Spruce, L.W.; Pfahl, M.; Fanjul, A.; Tachdjian, C.; Al-Shamma, H.A.; Pleynet, D.P.M.; Wiemann, T.R.; Ibarra, J.B. (Maxia Pharmaceuticals, Inc.); Heterocyclic derivs. for the treatment of cancer and other proliferative diseases. WO 02/072009 .
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) 25313 4-bromophenol 106-41-2 C6H5BrO 详情 详情
(II) 52642 1-Adamantanol; 1-Hydroxyadamantane; Tricyclo[3.3.1.1]decan-1-ol 768-95-6 C10H16O 详情 详情
(III) 59536 2-(1-adamantyl)-4-bromophenol C16H19BrO 详情 详情
(IV) 59537 1-(5-bromo-2-methoxyphenyl)adamantane; 2-(1-adamantyl)-4-bromophenyl methyl ether C17H21BrO 详情 详情
(V) 61340 3-(1-adamantyl)-4-{[tert-butyl(dimethyl)silyl]oxy}phenylboronic acid C22H35BO3Si 详情 详情
(VI) 61343 6-bromonicotinaldehyde C6H4BrNO 详情 详情
(VII) 61341 6-(3-(1-adamantyl)-4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)nicotinaldehyde C28H37NO2Si 详情 详情
(VIII) 61342 6-[3-(1-adamantyl)-4-hydroxyphenyl]nicotinaldehyde C22H23NO2 详情 详情
(IX) 10883 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione 2295-31-0 C3H3NO2S 详情 详情
Extended Information