%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