期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 23, 页码 17257-17264出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02325
关键词
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资金
- EPSRC MoSMed CDT [EP/S022791/1]
- AstraZeneca
- Cancer Research UK [C2115/A21421]
DNA-encoded libraries are efficient for identifying ligands for protein targets, and incorporating arylamines is desirable. By applying micellar technology to DNA chemistry for the Buchwald-Hartwig reaction, a robust method for synthesizing DNA-conjugated aryl and heteroarylamines has been developed.
DNA-encoded libraries are a very efficient means of identifying ligands for protein targets in high throughput. To fully maximize their use, it is essential to be able to carry out efficient reactions on DNA-conjugated substrates. Arylamines are privileged motifs in druglike molecules, and methods for their incorporation into DNA-encoded libraries are highly desirable. One of the preferred methods for their preparation, the Buchwald-Hartwig coupling, does not perform well on DNA conjugates using current approaches. We report the application of our recently developed micellar technology for on-DNA chemistry to the Buchwald-Hartwig reaction. Optimization of conditions led to a robust, high-yielding method for the synthesis of DNA-conjugated aryl and heteroarylamines, which is broad in substrate scope for both the arylamine and the DNA-conjugated aryl halide and is fully compatible with DNA-encoding and decoding procedures. This method will enable the preparation of diverse, high-fidelity libraries of biarylamines.
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