Cesium carbonate → Methyl 4-{1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethenyl}benzoate

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A microwave vial was charged with methyl 4-[1-(5-bromo-1,3-thiazol-2-yl)-ethenyl]benzoate (INTERMEDIATE 89, 0.225 g, 0.694 mmol), N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (INTERMEDIATE 3, 0.263 g, 0.694 mmol), Pd2(dba)3 (0.032 g, 0.035 mmol), cesium carbonate (0.452 g, 1.388 mmol) and X-Phos (0.033 g, 0.069 mmol). The vial was sealed and purged with Argon gas. Dioxane (2.43 mL) and water (0.24 mL) were added and the mixture was stirred at 60° C. for 75 minutes. The temperature was increased to 90° C. and reacted overnight. The resulting solution was cooled and filtered through a celite plug, washing with EtOAc and then concentrated. Chromatography on silica gel (Biotage 100G SNAP, 10-65% EtOAc/hexanes) afforded methyl 4-{1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethenyl}benzoate (103 mg, 0.207 mmol, 29.9% yield). MS ESI: [M+H]+ m/z 497.0.

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