Indazoles: regioselective protection and subsequent amine coupling reactions.
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.
Slade
David J
DJ
Department of Chemistry, Inspire Pharmaceuticals, Inc., 4222 Emperor Boulevard, Durham, North Carolina 27713, USA. drslade@gmail.com
Pelz
Nicholas F
NF
Bodnar
Wanda
W
Lampe
John W
JW
Watson
Paul S
PS
D000588:Amines / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007191:Indazoles / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013816:Thermodynamics
D000588:Amines; D007191:Indazoles