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【结 构 式】 
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【分子编号】51498 【品名】2-(4-iodophenyl)-2-[(trimethylsilyl)oxy]propanenitrile 【CA登记号】 |
【 分 子 式 】C12H16INOSi 【 分 子 量 】345.25515 【元素组成】C 41.75% H 4.67% I 36.76% N 4.06% O 4.63% Si 8.13% |
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：(II)Addition of cyanotrimethylsilane to 4'-iodoacetophenone (I) provided the O-silylated cyanohydrin (II), which was subsequently reduced to the amino alcohol (III) employing borane-dimethyl sulfide complex. Acylation of (III) with 2-propanesulfonyl chloride gave sulfonamide (IV). The hydroxyl group of (IV) was then fluorinated by means of diethylaminosulfur trifluoride, and the resultant racemic fluoride was resolved by chiral HPLC. Finally, Suzuki coupling of the required (S)-enantiomer (V) with boronic ester (VI) yielded the title biphenyl derivative.
| 【1】 Jones, W.D.; Mitchell, D.; Fray, A.H.; Miller, W.D.; Cantrell, B.E.; Bender, D.M.; Zimmerman, D.M.; Simon, R.L.; Zarrinmayeh, H. (Eli Lilly and Company); Monofluoroalkyl derivs.. EP 1183232; WO 0066546 . |
| 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) | 51497 | 4'-Iodoacetophenone; 4-Iodoacetophenone; 1-(4-Iodophenyl)ethanone | 13329-40-3 | C8H7IO | 详情 | 详情 |
| (II) | 51498 | 2-(4-iodophenyl)-2-[(trimethylsilyl)oxy]propanenitrile | C12H16INOSi | 详情 | 详情 | |
| (III) | 51499 | 1-amino-2-(4-iodophenyl)-2-propanol | C9H12INO | 详情 | 详情 | |
| (IV) | 51500 | N-[2-hydroxy-2-(4-iodophenyl)propyl]-2-propanesulfonamide | C12H18INO3S | 详情 | 详情 | |
| (V) | 51501 | N-[(2S)-2-fluoro-2-(4-iodophenyl)propyl]-2-propanesulfonamide | C12H17FINO2S | 详情 | 详情 | |
| (VI) | 51502 | N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide | C13H20BNO4S | 详情 | 详情 |
Extended Information