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General synthetic routes to analogs 13 to 36. Reagents and conditions: step a, 3-iodo-1-methyl-1H-indazole-5-carboxylic acid, HATU, DIEA, DMF, rt, 16 h, 71 to 95%; step b, boronic acid derivative, Pd(dppf)Cl2·CH2Cl2 (10 mol%), DME/Na2CO3(sat) (vol/vol, 1:1), microwave 90 to 110 °C, 1 h, 29 to 95%; step c, for ester only: LiOH·H2O, THF, H2O, 45 °C, 16 h; step d, RNH2, HATU, DIEA, DMF, rt, 16 h; step e, for N-Boc deprotection only: 4 N HCl, 1,4-dioxane, rt, 1 h, 14 to 91% (three steps).
