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Regioselective protection and subsequent amine coupling reactions
Slade, D. J., Pelz, N. F., Bodnar, W., Lampe, J. W., & Watson, P. S. (2009). Indazoles: Regioselective protection and subsequent amine coupling reactions. The Journal of Organic Chemistry, 74(16), 6331-6334. https://doi.org/10.1021/jo9006656
Indazoles are unselectively protected under strongly basic conditions to give a mixture at N-1 and N-2. Under mildly acidic conditions, regioselective protection at N-2 takes place. Thermodynamic conditions lead to regioselective protection at N-1. This trend applies to various substituted indazoles. Protected 5-bromoindazoles participate in Buchwald reactions with a range of amines to generate novel derivatives.