【结 构 式】 |
【分子编号】62808 【品名】N-(4,6-dimethyl-2,3-dihydro-1H-indol-7-yl)-2,2-dimethylpropanamide 【CA登记号】 |
【 分 子 式 】C15H22N2O 【 分 子 量 】246.35256 【元素组成】C 73.13% H 9% N 11.37% O 6.49% |
合成路线1
该中间体在本合成路线中的序号:(VIII)4,6-Dimethylindole (I) is reduced to the corresponding indoline (II) with NaBH3CN in AcOH. After acylation with Ac2O, the resultant N-acetylindoline (III) is brominated by means of Br2 in AcOH to give the 5-bromoindoline derivative (IV). Nitration of (IV) with fuming HNO3 in H2SO4/AcOH provides the 7-nitro indoline (V). Then, simultaneous debromination and nitro group reduction in (V) is accomplished by hydrogenation in the presence of Pd/C to furnish aniline (VI). Further acylation of (VI) with pivaloyl chloride leads to diamide (VII). The N-acetyl group of (VII) is selectively removed under alkaline hydrolysis conditions to yield indoline (VIII). Finally, alkylation of (VIII) with 1-bromodecane and K2CO3 furnishes the title compound.
【1】 Yoshimi, A.; Kasai, M.; Shirahase, H.; Matsui, H.; Kanda, M.; Kurahashi, K.; Kamiya, S.; Takahashi, K.; Nakamura, S.; Bioavailable acyl-CoA: Cholesterol acyltransferase inhibitor with anti-peroxidative activity: Synthesis and biological activity of novel indolinyl amide and urea derivatives. Chem Pharm Bull 2000, 48, 6, 817. |
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) | 40795 | 4,6-dimethyl-1H-indole | C10H11N | 详情 | 详情 | |
(II) | 40796 | 4,6-dimethylindoline | C10H13N | 详情 | 详情 | |
(III) | 40797 | 1-(4,6-dimethyl-2,3-dihydro-1H-indol-1-yl)-1-ethanone | C12H15NO | 详情 | 详情 | |
(IV) | 40798 | 1-(5-bromo-4,6-dimethyl-2,3-dihydro-1H-indol-1-yl)-1-ethanone | C12H14BrNO | 详情 | 详情 | |
(V) | 40799 | 1-(5-bromo-4,6-dimethyl-7-nitro-2,3-dihydro-1H-indol-1-yl)-1-ethanone | C12H13BrN2O3 | 详情 | 详情 | |
(VI) | 62806 | 1-(7-amino-4,6-dimethyl-2,3-dihydro-1H-indol-1-yl)-1-ethanone | C12H16N2O | 详情 | 详情 | |
(VII) | 62807 | N-(1-acetyl-4,6-dimethyl-2,3-dihydro-1H-indol-7-yl)-2,2-dimethylpropanamide | C17H24N2O2 | 详情 | 详情 | |
(VIII) | 62808 | N-(4,6-dimethyl-2,3-dihydro-1H-indol-7-yl)-2,2-dimethylpropanamide | C15H22N2O | 详情 | 详情 |