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【结 构 式】 
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【分子编号】64046 【品名】6-bromo-1-chloro-2,3-dihydro-1H-indene 【CA登记号】 |
【 分 子 式 】C9H8BrCl 【 分 子 量 】231.51922 【元素组成】C 46.69% H 3.48% Br 34.51% Cl 15.31% |
合成路线1
该中间体在本合成路线中的序号：(IX)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)
| 【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 |