The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Jul. 11, 2017

Filed:

Jul. 28, 2014
Applicant:

The Regents of the University of California, Oakland, CA (US);

Inventors:

John Hartwig, Berkeley, CA (US);

Patrick Fier, Berkeley, CA (US);

Assignee:
Attorneys:
Primary Examiner:
Int. Cl.
CPC ...
C07D 493/00 (2006.01); C07D 213/61 (2006.01); C07D 401/04 (2006.01); C07D 239/46 (2006.01); C07D 213/63 (2006.01); C07D 213/65 (2006.01); C07D 213/75 (2006.01); C07D 213/79 (2006.01); C07D 213/80 (2006.01); C07D 213/803 (2006.01); C07D 213/81 (2006.01); C07D 213/82 (2006.01); C07D 215/18 (2006.01); C07D 239/42 (2006.01); C07D 405/04 (2006.01);
U.S. Cl.
CPC ...
C07D 213/61 (2013.01); C07D 213/63 (2013.01); C07D 213/65 (2013.01); C07D 213/75 (2013.01); C07D 213/79 (2013.01); C07D 213/80 (2013.01); C07D 213/803 (2013.01); C07D 213/81 (2013.01); C07D 213/82 (2013.01); C07D 215/18 (2013.01); C07D 239/42 (2013.01); C07D 239/46 (2013.01); C07D 401/04 (2013.01); C07D 405/04 (2013.01);
Abstract

The present invention provides compositions and methods for the selective C—H fluorination of nitrogen-containing heteroarenes with AgF, which has previously been considered too reactive for practical, selective C—H fluorination. Fluorinated heteroarenes are prevalent in numerous pharmaceuticals, agrochemicals and materials. However, the reactions used to introduce fluorine into these molecules require pre-functionalized substrates or the use of Fgas. The present invention provides a mild and general method for the C—H fluorination of nitrogen-containing heteroarene compounds to 2-fluoro-heteroarenes with commercially available AgF. In various embodiments, these reactions occur at ambient temperature within one hour and occur with exclusive selectivity for fluorination at the 2-position. Exemplary reaction conditions are effective for fluorinating diazine heteroarenes to form a single fluorinated isomer.


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