面向洛替利普隆的致密官能化苯并二恶茂中间体的无过渡金属合成
IF 3.5
3区 化学
Q2 CHEMISTRY, APPLIED
引用次数: 0
摘要
本文描述了一种十克级制备关键中间体(±)-2-(4-溴-2-甲基苯并[d][1,3]二恶茂-2-基)-5-氯吡啶的方法。关键步骤包括用 2,2-二氯丙酸甲酯对 3-溴邻苯二酚进行双亲核取代，使用 Weinreb 酰胺促进从羧酸中生成酮，以及从乙脒盐中从头构建取代的氯吡啶。工艺的发展使我们能够在 5 个步骤后分离出多克的最终产品，收率为 34%，且无需色谱法。本文章由计算机程序翻译，如有差异，请以英文原文为准。
Transition-Metal-Free Synthesis of a Densely Functionalized Benzodioxole Intermediate toward Lotiglipron
A decagram-scale preparation of the key intermediate (±)-2-(4-bromo-2-methylbenzo[d][1,3]dioxol-2-yl)-5-chloropyridine is described. Key steps involve a double nucleophilic substitution of 3-bromocatechol with methyl 2,2-dichloropropanoate, use of a Weinreb amide to facilitate the formation of a ketone from a carboxylic acid, and de novo construction of a substituted chloropyridine from a vinamidinium salt. Process developments enabled isolation of multigram quantities of final product in 34% yield after 5 steps and no chromatography.
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来源期刊
CiteScore
6.90
自引率
14.70%
发文量
251
审稿时长
2 months
期刊介绍：
The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.
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