A solution of Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, Mo., 0.165 g, 0.233 mmol), tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (ASW Medchem, Brunswick, N.J., 1.254 g, 3.49 mmol), 1-(2-bromo-5-(trifluoromethyl)phenyl)-5-methyl-1H-imidazole (derived above, 0.710 g, 2.327 mmol), and potassium phosphate (1.976 g, 9.31 mmol) in 10 mL dioxane 5 mL water was heated to 120° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc and the organics were concentrated. The resulting residue was purified by silica gel column chromatography (0 to 100% EtOAc/heptane) yielding tert-butyl 5-(2-(5-methyl-1H-imidazol-1-yl)-4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.450 g, 0.984 mmol).
