Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 23, Pages 11631-11643Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502288q
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Funding
- Eli Lilly and Company
- NIH [GM096129]
- Alfred P. Sloan Foundation
- Camille and Henry Dreyfus Foundation
- University of Michigan
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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.
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