第 51 卷第 6 期 | ![](image2/wentou.gif) | Vol. 51 No. 6 | 2021 年 12 月 | Dec 2021 |
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所属栏目:医药及中间体
5一三娠甲基时啋啾的合成 |
胡 涛, 罗宏军, 梁慧兴
(扬子江药业集团有限公司, 江苏 泰州 225321)
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摘 要:
报道了 5-三氯甲基呏啋淋的一种合成新方法, 即以对三氯甲基苯胺(1)为起始原朴, 引入甲磺酰
基保护胺基, 经芳环殃代反应生成 N-(2-殃-4-三氯甲基苯基)甲磺酰胺(3), 然后与三甲基乙块基硅一锅法进行 Sonogashira 偶联和环化反应生成取代呏啋(4a)、 (4b),
在强碱作用下一锅法脱去 Ms 保护基和 TMS 生成呏啋(5), 最后经氛基硐氢化钠还原成 5-三氯甲基呏啋淋(TM), 历经 5 步反应, 总收率为 40%, 中间体和目标产物结构经 1H
NMR 和 MS 确证。
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关键词:
对三氯甲基苯胺; 三甲基乙块基硅; 5-三氯甲基咐啋咏; 一锅法合成
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中图分类号:TQ463 文献标识码:A 文章编号:1009-9212(2021)06-0032-03 |
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Synthesis of 5-(Trifluoromethyl)indoline
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HU Tao, LUO Hong-jun, LIANG Hui-xing
(Yangtze River Pharmaceutical Group Co.,Ltd., Taizhou 225321, China)
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Abstract:A novel synthetic approach of 5-(trifluoromethyl)indoline was described. Starting from
p-trifluoromethyl aniline 1, the N-methanesulfonation product 2 was iodinated and then was coupled
with Trimethylsilylacetylene in the presence of Pd catalyst, which gave one-pot cyclization product
N-methanesulfonyl-lH-indole 4a and 4b. The following one-pot de-Ms and de-TMS group produced
5-trifluoromethyl-lH-indole (5) in the presence of strong base, which was reduced into the title
compound TM. The total 5 -step reactions gave an overall 40% yields. The related intermediates and
compounds were confirmed by lH NMR and MS.
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Key words:
p-trifluoromethyl aniline; Trimethylsilylacetylene; 5-(trifluoromethyl)indoline; one-pot synthesis
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作者简介:
胡 涛(1975—),男,河南信阳人,高级工程师,博士,主要从事药物合成及工艺开发研究(E-mail hutao@yangzijiang.com)。
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收稿日期:2021-10-2
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