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Methods for fluorinating compounds

A technology of fluorination and tetramethylammonium fluoride, applied in the field of fluorinated compounds, can solve the problems of poor substrate selectivity and reactivity, expensive stoichiometric reagents, etc.

Active Publication Date: 2022-01-04
DOW AGROSCIENCES LLC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although these methods have been successful in some systems, they have limitations such as poor selectivity and reactivity for certain substrates
These methods also require the use of expensive stoichiometric reagents (C 6 f 6 , NHC), making it impossible to implement on an industrial scale

Method used

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  • Methods for fluorinating compounds
  • Methods for fluorinating compounds
  • Methods for fluorinating compounds

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Embodiment

[0204] The following examples are set forth below to illustrate methods, compositions and results in accordance with the disclosed subject matter. These examples are not intended to be inclusive of all aspects of the subject matter disclosed herein, but are intended to illustrate representative methods, compositions, and results. These examples are not intended to exclude equivalents and modifications of the invention which are obvious to those skilled in the art.

[0205] While efforts have been made to ensure accuracy with respect to numbers (eg, amounts, temperature, etc.), some errors and deviations should be accounted for. Unless indicated otherwise, parts are parts by weight, temperature is in °C or is at ambient temperature, and pressure is at or near atmospheric. There are many variations and combinations of reaction conditions, eg, component concentrations, temperatures, pressures, and other reaction ranges and conditions that can be used to optimize the product puri...

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Abstract

This paper discloses the use of NMe 4 S of various halide and sulfonate substituted aryl and heteroaryl substrates performed by F at mild temperatures (e.g., 0 to 80 °C) N Ar fluorinated.

Description

technical field [0001] This application generally relates to methods of fluorinating compounds and to fluorinating compounds. Background technique [0002] Fluorinated organic molecules are increasingly used in the life sciences industry. The presence of fluorine substituents can have a positive effect on the biological properties of the compound. Substitution of hydrogen atoms by fluorine atoms in biologically active molecules generally confers improved bioavailability and / or metabolic stability. However, despite the importance of incorporating fluorine into organic molecules, there are relatively few selective and mild synthetic methods for C–F bond formation, especially at process scale. Synthetic techniques for fluorinating compounds are therefore an area of ​​significant interest. [0003] A method for the industrial preparation of aryl and heteroaryl fluorides is the nucleophilic aromatic fluorination (S N Ar) or halex fluorination (Adams, D.J. et al., Chem. Soc. R...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/26
CPCC07D213/26C07D215/18C07D215/26C07D217/22C07D237/12C07D241/16C07D213/76C07D213/79C07D213/803C07D213/84C07D213/85C07D215/04C07D217/02C07D237/08
Inventor M·桑福德S·赖安S·斯奇米勒Y·程D·布兰德
Owner DOW AGROSCIENCES LLC