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