Scheme 1. Preparation of Compounds 3–7.

Reagents and conditions: (i) 1. H₂SO₄ (aq), 1,4-dioxane, RT. 2. HNO₃, H₂SO₄, 0 °C; (ii) 1. (Boc)₂O, CH₂Cl₂, RT. 2. H₂, Pd/C, MeOH, RT; (iii) 11, EDC, HOBT, Et₃N, CH₂Cl₂, RT; or 4-bromobenzoyl chloride, NEt₃, CH₂Cl₂, RT; (iv) 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole or 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester, Pd(PPh₃)₄, Na₂CO₃, H₂O, DME, reflux; (v) HCl, 1,4-dioxane, EtOAc, RT; (vi) PhNH₂, NEt₃, CH₂Cl₂, RT; (vii) N-Boc-3-hydroxy-1-propylamine, Cs₂CO₃, DMF, 60 °C; (viii) 3-amino-5-methoxyphenol, Pd₂dba₃, XPhos, K₃PO₄, DME, 140 °C. For yields, see experimental procedures in Supporting Information.