N,N-dimethyl-6-[2-(trimethylsilyl)ethynyl]-2,3-dihydro-1H-inden-1-amine; N,N-dimethyl-N-{6-[2-(trimethylsilyl)ethynyl]-2,3-dihydro-1H-inden-1-yl}amine -Drug Synthesis Database

【结构式】

【分子编号】64048

【品名】N,N-dimethyl-6-[2-(trimethylsilyl)ethynyl]-2,3-dihydro-1H-inden-1-amine; N,N-dimethyl-N-{6-[2-(trimethylsilyl)ethynyl]-2,3-dihydro-1H-inden-1-yl}amine

【CA登记号】

【分子式】C₁₆H₂₃NSi

【分子量】257.45086

【元素组成】C 74.65% H 9% N 5.44% Si 10.91%

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：(XII)

6-Bromo-1-indanone (VII) is reduced to alcohol (VIII) employing NaBH4. After chlorination of (VIII) with SOCl2, the resultant alkyl chloride (IX) is displaced by heating with ethanolic dimethylamine in a sealed vessel to produce the (dimethylamino)indan (X). Palladium-catalyzed coupling of aryl bromide (X) with trimethylsilyl acetylene (XI) furnishes the silyl acetylene (XII), which is then desilylated to (XIII) with Bu4NF in THF. Finally, condensation between acetylene (XIII), aryl iodide (VI) and carbon monoxide in the presence of palladium catalyst leads to the title quinolone derivative. (1,2)

参考文献中间体

合成目标

【1】 Dhar, T.G.M.; Watterson, S.H.; Chen, P.; Shen, Z.; Gu, H.H.; Norris, D.; Carlsen, M.; Haslow, K.D.; Pitts, W.J.; Guo, J.; Chorba, J.; Fleener, C.A.; Rouleau, K.A.; Townsend, R.; Hollenbaugh, D.; Iwanowicz, E.J.; Quinolone-based IMPDH inhibitors: Introduction of basic residues on ring D and SAR of the corresponding mono, di and benzofused analogues. Bioorg Med Chem Lett 2003, 13, 3, 547.
【2】 Pitts, W.J.; Iwanowicz, E.J.; Dhar, T.G.M.; Gu, H.H.; Watterson, S.H. (Bristol-Myers Squibb Co.); Heterocycles that are inhibitors of IMPDH enzyme. EP 1276739; JP 2003531205; WO 0181340 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	64043	2-iodo-5-(methyloxy)-4-(1,3-oxazol-5-yl)aniline; 2-iodo-5-(methyloxy)-4-(1,3-oxazol-5-yl)phenylamine		C₁₀H₉IN₂O₂	详情	详情
(VII)	64044	6-bromo-2,3-dihydro-1H-inden-1-one		C₉H₇BrO	详情	详情
(VIII)	64045	6-bromo-2,3-dihydro-1H-inden-1-ol		C₉H₉BrO	详情	详情
(IX)	64046	6-bromo-1-chloro-2,3-dihydro-1H-indene		C₉H₈BrCl	详情	详情
(X)	64047	6-bromo-N,N-dimethyl-2,3-dihydro-1H-inden-1-amine; N-(6-bromo-2,3-dihydro-1H-inden-1-yl)-N,N-dimethylamine		C₁₁H₁₄BrN	详情	详情
(XI)	23897	ethynyl(trimethyl)silane；trimethylsilyl acetylene	1066-54-2	C₅H₁₀Si	详情	详情
(XII)	64048	N,N-dimethyl-6-[2-(trimethylsilyl)ethynyl]-2,3-dihydro-1H-inden-1-amine; N,N-dimethyl-N-{6-[2-(trimethylsilyl)ethynyl]-2,3-dihydro-1H-inden-1-yl}amine		C₁₆H₂₃NSi	详情	详情
(XIII)	64049	N-(6-ethynyl-2,3-dihydro-1H-inden-1-yl)-N,N-dimethylamine; 6-ethynyl-N,N-dimethyl-2,3-dihydro-1H-inden-1-amine		C₁₃H₁₅N	详情	详情

Extended Information