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【结 构 式】 
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【分子编号】64334 【品名】6-(methyloxy)-5-(1,3-oxazol-5-yl)-1,3-dihydro-2H-indol-2-one 【CA登记号】 |
【 分 子 式 】C12H10N2O3 【 分 子 量 】230.22308 【元素组成】C 62.61% H 4.38% N 12.17% O 20.85% |
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：(IV)Condensation of iodoaniline (I) with ethyl 2-(methylsulfanyl)acetate (II) in the presence of sulfuryl chloride gives rise to the oxindole derivative (III). Desulfuration of (III) by means of Raney-nickel then affords (IV). The Vilsmeier-Haack reaction of oxindole (IV) with POBr3 and DMF leads to the bromo aldehyde (V). This is finally subjected to Suzuki coupling with 3-benzothienylboronic acid (VI) to furnish the title compound.
| 【1】 Watterson, S.H.; Dhar, T.G.M.; Ballentine, S.K.; Shen, Z.; Barrish, J.C.; Cheney, D.; Fleener, C.A.; Rouleau, K.A.; Townsend, C.; Hollenbaugh, D.L.; Iwanowicz, E.J.; Novel indole-based inhibitors of IMPDH: Introduction of hydrogen bond acceptors at indole C-3. Bioorg Med Chem Lett 2003, 13, 7, 1273. |
| 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) | 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 | |
| (II) | 48543 | Ethyl methylthioacetate; (Methylthio)acetic acid ethyl ester; ethyl 2-(methylsulfanyl)acetate | 4455-13-4 | C5H10O2S | 详情 | 详情 |
| (III) | 64333 | 6-(methyloxy)-3-(methylsulfanyl)-5-(1,3-oxazol-5-yl)-1,3-dihydro-2H-indol-2-one | C13H12N2O3S | 详情 | 详情 | |
| (IV) | 64334 | 6-(methyloxy)-5-(1,3-oxazol-5-yl)-1,3-dihydro-2H-indol-2-one | C12H10N2O3 | 详情 | 详情 | |
| (V) | 64335 | 2-bromo-6-(methyloxy)-5-(1,3-oxazol-5-yl)-1H-indole-3-carbaldehyde | C13H9BrN2O3 | 详情 | 详情 | |
| (VI) | 64336 | 1-benzothiophen-3-ylboronic acid | C8H7BO2S | 详情 | 详情 |
Extended Information