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Alkylamino coupling reactions at the C4 positions of 4-halo-1 H -1-tritylpyrazoles were investigated using palladium or copper catalysts. The Pd(dba) 2 catalyzed C-N coupling reaction of aryl- or alkylamines, lacking a β-hydrogen atom, proceeded smoothly using  t  BuDavePhos as a ligand. As a substrate, 4-Bromo-1-tritylpyrazole was more effective than 4-iodo or chloro-1-tritylpyrazoles. Meanwhile, the CuI mediated C-N coupling reactions of 4-iodo-1 H -1-tritylpyrazole were effective for alkylamines possessing a β-hydrogen atom.

C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)2 or CuI