10.1021/jo502288q.s001 James J. Douglas James J. Douglas Kevin P. Cole Kevin P. Cole Corey R. J. Stephenson Corey R. J. Stephenson Photoredox Catalysis in a Complex Pharmaceutical Setting: Toward the Preparation of JAK2 Inhibitor LY2784544 American Chemical Society 2015 methylation reaction JAK 2 Inhibitor LY 2784544We report investigation Photoredox Catalysis photoredox reactions Complex Pharmaceutical bond construction optimized reaction unfunctionalized pyridazine 2015-12-17 06:09:06 Journal contribution https://acs.figshare.com/articles/journal_contribution/Photoredox_Catalysis_in_a_Complex_Pharmaceutical_Setting_Toward_the_Preparation_of_JAK2_Inhibitor_LY2784544/2044806 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 <i>N</i>-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 <i>N</i>-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.