• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【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%

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:(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
Extended Information