Decagram Scale Synthesis and Deployment of a Picolinamide Ligand for a Copper-Catalyzed C–N Cross-Coupling

IF 3.3 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2026-10-16 Epub Date: 2026-10-07 DOI:10.1021/acs.oprd.6c00198

Andrew McGrath, Dan Lehnherr

引用次数: 0

Abstract

The synthesis of a picolinamide ligand is demonstrated on a 70 g scale in a process-friendly solvent, and its application in a copper-catalyzed C–N cross-coupling on a 20 g scale is reported. The ligand can be accessed in one step via an amide coupling using inexpensive, commercially available 6-hydroxypicolinic acid and 6-methylquinolin-5-amine. A simple aqueous workup followed by a pH-swing-induced crystallization affords the ligand without the need for column chromatography. The combination of the scalable access to the ligand and its excellent performance in copper-catalyzed C–N cross-coupling on decagram scale renders this ligand attractive for deployment in process chemistry applications.

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铜催化C-N交叉偶联吡啶胺配体的合成与部署

摘要：在70 g条件下，在工艺友好型溶剂中合成了一种吡啶酰胺配体，并报道了其在20 g条件下铜催化的C-N交叉偶联反应中的应用。该配体可以通过使用廉价的、市售的6-羟基喹啉酸和6-甲基喹啉-5-胺的酰胺偶联一步获得。一个简单的水处理，然后是ph振荡诱导结晶，提供配体，而不需要柱层析。配体的可扩展访问及其在铜催化的十元尺度上的C-N交叉偶联的优异性能使该配体在过程化学应用中具有吸引力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Process Research & Development 化学-应用化学

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.