Scheme 2. (A) Indazole alkylation using standard alkylation conditions. Crude 2a : 3a ratio was 58 : 42 by LCMS (225 nm). (B) HTE study and selectivity results in a heat map. Standard conditions stirred 15 mg 1a, 1.1 equiv. base, 1 equiv. reagent, and 300 μL solvent at 50 °C for 16 h. DMAP = 4-dimethylaminopyridine; TBD = triazabicyclodecene. (C) Workflow followed leading to reprioritisation of resourcing.
