Indazoles: Regioselective protection and subsequent amine coupling reactions

DOI: 10.1021/jo9006656

Source and publish data:

Journal of Organic Chemistry p. 6331 - 6334 (2009)

Update date:2022-08-15

Topics:

Authors:

Slade, David J.

Pelz, Nicholas F.

Bodnar, Wanda

Lampe, John W.

Watson, Paul S.

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Article abstract of DOI:10.1021/jo9006656

(Chemical Equation Presented) 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.

Full text of DOI:10.1021/jo9006656

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