Combine RuPhos Palladium(II) phenethylamine chloride (60 μmol, 43 mg), dioxane (0.5 mL) and potassium tert-butoxide (1 M tetrahydrofuran, 60 μmol, 60 μL) under nitrogen, sonicate the mixture for 0.5 minute. Add the Ruphos catalyst mixture to a reaction vessel under nitrogen containing 6-bromo-3-(5-fluoropyrimidin-4-yl)-2-[(1R)-1-(4-methoxyphenyl)ethyl]-3-methyl-isoindolin-1-one (544 mg, 1.192 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate (1.79 mmol, 526 mg), 1,4-dioxane (6 mL), sodium carbonate (3.6 mmol, 2.4 mL 1.5 M aqueous) and heat in a microwave at 150° C. for 30 minutes. Dilute the mixture with ethyl acetate, wash with aqueous 1.5 M sodium carbonate, wash with saturated aqueous sodium chloride, dry over magnesium sulfate, filter through diatomaceous earth, and evaporate to a light yellow residue. Dissolve the residue in anisole (1 mL) and trifluoroacetic acid (7 mL) and heat to 80° C. for 4 hours, then heat to 70° C. for 18 hours. Evaporate the mixture under reduced pressure, dissolve in methanol, load on a 10 g SCX column, wash with methanol (100 mL), elute with 2 M ammonia in methanol and evaporate. Purify on 40 g silica gel with a gradient of 1-8% methanol/dichloromethane to give the title compound as a white foam (279 mg, 76%). ES/MS m/z: 310 (M+H).
