In a 10 mL reaction vial, 1-methyl-1H-indazol-5-ylboronic acid (31 mg, 0.173 mmol) and (S)-ethyl 2-(2-(4-bromothiazol-2-yl)-7-(4chlorophenyl)-5methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (100 mg, 0.173 mmol) were mixed with dioxane (5 mL) and water (1 mL). The resulting reaction mixture was bubbled with argon for 5 min. Then potassium carbonate (60 mg, 0.432 mmol) and Pd(PPh3)4 were added sequentially. The reaction mixture was sealed and heated in oil bath at 95° C. for 2 h. The brown mixture was then diluted with EtOAc (20 mL), filtered and the filtrate was concentrated and purified on silica gel column with 0-30% EtOAc/Hex to afford the title compound. LCMS-ESI+: calc'd for: C33H31ClN4O3S2: 631.2, 633.2, 632.2 (M+H+); found: 631.0, 633.1, 632.1 (M+H+).
