1-chloro-4-(trimethylsilyl)-3-butyn-2-one -Drug Synthesis Database

【结构式】

【分子编号】63351

【品名】1-chloro-4-(trimethylsilyl)-3-butyn-2-one

【CA登记号】

【分子式】C₇H₁₁ClOSi

【分子量】174.70194

【元素组成】C 48.13% H 6.35% Cl 20.29% O 9.16% Si 16.08%

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：(III)

Chloroacetyl chloride (I) is condensed with bis(trimethylsilyl)acetylene (II) in the presence of AlCl3 to provide 1-chloro-4-(trimethylsilyl)-3-butyn-2-one (III). Cyclization of chloro ketone (III) with thioacetamide (IV) affords the ethynylthiazole derivative (V). Finally, palladium-catalyzed coupling of (V) with 3-bromopyridine (VI) gives rise to the target diarylacetylene.

参考文献中间体

合成目标

【1】 Cosford, N.D.P.; Tehrani, L.; Roppe, J.; Schweiger, E.; Smith, N.D.; Anderson, J.; Bristow, L.; Brodkin, J..; Jiang, X.; McDonald, I.; Rao, S.; Washburn, M.; Varney, M.A.; 3-[(2-Methyl-1,3-thiazol-4-yl)ethynyl]- pyridine: A potent and highly selective metabotropic glutamate subtype 5 receptor antagonist with anxiolytic activity. J Med Chem 2003, 46, 2, 204.
【2】 McDonald, I.A.; Munoz, B.; Vernier, J.-M.; Cosford, N.D.P.; Varney, M.A.; Hess, S.D.; Bleicher, L.S.; Cube, R.V.; Schweiger, E.J. (Merck & Co., Inc.); Heterocyclic cpds. and methods of use thereof. JP 2003508390; WO 0116121 .

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)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(II)	27189	trimethyl[2-(trimethylsilyl)ethynyl]silane	14630-40-1	C₈H₁₈Si₂	详情	详情
(III)	63351	1-chloro-4-(trimethylsilyl)-3-butyn-2-one		C₇H₁₁ClOSi	详情	详情
(IV)	19170	ethanethioamide	62-55-5	C₂H₅NS	详情	详情
(V)	63352	2-methyl-4-[2-(trimethylsilyl)ethynyl]-1,3-thiazole		C₉H₁₃NSSi	详情	详情
(VI)	13265	3-Bromopyridine	626-55-1	C₅H₄BrN	详情	详情

Extended Information