Methods of Fluorinating Compounds

Abstract

A method of preparing a fluorinated aryl or heteroaryl substrate by mixing a quaternary ammonium cyanide and an aryl or heteroaryl substrate substituted with at least one chlorine, bromine, sulfonyl, or nitro group to obtain a mixture, and The mixture is mixed with hexafluorobenzene to obtain the fluorinated substrate.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of US Provisional Patent Application 61 / 902,979, filed November 12, 2013, and US Provisional Patent Application 61 / 985,224, filed April 28, 2014, the entire disclosures of which are expressly incorporated herein by reference. technical field [0003] This application relates generally to methods of fluorinating aryl or heteroaryl compounds and the fluorinated compounds. Background technique [0004] Fluorinated organic molecules are increasingly used in the life sciences industry. The presence of fluorine substituents may have a positive effect on the biological properties of the compounds. Synthetic techniques for fluorinating compounds are therefore an important area of ​​interest. [0005] Selective fluorination of aryl and heteroaryl substrates is a challenging synthetic problem. For example, monochloro- and dichloro-substituted picolinates are difficult to fluorinate and requ...

AI Technical Summary

Problems solved by technology

[0007] Although TBAF* has been successfully used in some systems, it still has limitations, such as poor selectivity and reactivity for difficult-to-fluorinate substrates such as chloropyridines, especially the 6-arylpicolinate family

Other limitations include that TBAF* must be pre-formed for each batch of reactions, and fluorination has only been demonstrated in DMSO

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