A microwave vial containing (S)-ethyl 2-(tert-butoxy)-2-(2-(2-chloro-5-(difluoromethyl)pyridin-4-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)acetate (44 mg, 0.076 mmol) was charged with (1-methyl-1H-indazol-5-yl)boronic acid (26 mg, 0.15 mmol), then Pd(PPh3)4 (18 mg, 0.02 mmol). The vial was flushed with argon, diluted with dioxane (1.0 mL) and to this was added 2M aqueous K2CO3 (0.15 mL, 0.30 mmol). The vial was sealed, heated to 120° C. for 3 hours, and then allowed to cool to room temperature. The mixture was diluted with EtOAc, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (10-40% EtOAc/Hex gradient) to afford the desired product. LCMS-ESI+: calc'd for C36H34ClF2N4O3S: 675.2 (M+H+); Found: 675.2 (M+H+).
