To a mixture of 2-(aminomethyl)-1,1,1-trifluoro-4-[5-fluoro-2-(methyloxy)phenyl]-4-methyl-2-pentanol (Intermediate 18, 49.5 mg, 0.16 mmol) and 4-bromo-1-(2-fluorophenyl)-6-methyl-1H-indazole (Intermediate 26, 45.8 mg, 0.15 mmol) in toluene (0.75 mL) were added tris(dibenzylideneacetone)dipalladium(0) (6.9 mg, 0.075 mmol), racemic-BINAP (9.3 mg, 0.015 mmol) and sodium tert-butoxide (18.5 mg, 0.192 mmol). The mixture was heated in a microwave at 120° C. for 30 min and then cooled and partitioned between water and dichloromethane. The organic layer was separated, dried and purified by silica gel chromatography using the Flashmaster II (20 g cartridge) eluting with a 0:100 cyclohexane:ethyl acetate gradient over 60 minutes to give crude product (43.6 mg) which was purified further by mass-directed autopreparation to give the title compound (18 mg).
