%0 Journal Article
%A Douglas, James
J.
%A Cole, Kevin P.
%A R. J. Stephenson, Corey
%D 2015
%T Photoredox Catalysis in a
Complex Pharmaceutical Setting:
Toward the Preparation of JAK2 Inhibitor LY2784544
%U https://acs.figshare.com/articles/journal_contribution/Photoredox_Catalysis_in_a_Complex_Pharmaceutical_Setting_Toward_the_Preparation_of_JAK2_Inhibitor_LY2784544/2044806
%R 10.1021/jo502288q.s001
%2 https://acs.figshare.com/ndownloader/files/3616122
%K methylation reaction
%K JAK 2 Inhibitor LY 2784544We report
%K investigation
%K Photoredox Catalysis
%K photoredox reactions
%K Complex Pharmaceutical
%K bond construction
%K optimized reaction
%K unfunctionalized pyridazine
%X We
report a detailed investigation into the application of visible
light-mediated photocatalysis to a challenging bond construction in
a complex pharmaceutical target. The optimized reaction allowed the
direct coupling of N-methylmorpholine with an unfunctionalized
pyridazine in good yield and selectivity, and with high purity of
the product isolated via crystallization. The reaction also facilitated
the expedient synthesis of a range of analogues via the use of other
commercially available N-methyl substituted tertiary
amines, and therefore it represents an attractive tool for medicinal
chemistry. Furthermore, a number of other interesting photoredox reactions
were discovered during the course of this investigation, such as a
formal methylation reaction via C–N bond cleavage, functionalization
of C–H bonds alpha to amides, and a visible light-mediated
iminium ion reduction.
%I ACS Publications