Synthesis of a Sodium–Hydrogen Exchange Type 1 Inhibitor: An Efficient Cu-Catalyzed Conjugated Addition of a Grignard Reagent to an Acetyl Pyridinium Salt

…, X Wei, D Byrne, A Chitroda, B Narayanan…

Index: Tang, Wenjun; Sarvestani, Max; Wei, Xudong; Nummy, Laurence J.; Patel, Nitinchandra; Narayanan, Bikshandarkoil; Byrne, Denis; Lee, Heewon; Yee, Nathan K.; Senanayake, Chris H. Organic Process Research and Development, 2009 , vol. 13, # 6 p. 1426 - 1430

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Abstract

A facile and economical five-step process for the synthesis of a sodium–hydrogen exchange type I inhibitor (NHE-1) was developed from readily available starting materials in 43% overall yield. Key transformations included a highly efficient copper-catalyzed conjugate addition of 2-trifluoromethylphenyl Grignard reagents to acetyl pyridinium salts, a facile hydrogenation of 4-aryl dihydropyridines, a regioselective aromatic bromination, an ...