Reaction Steps
A solution of Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, Mo., 0.014 g, 0.019 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (0.054 g, 0.242 mmol), 5-(2-bromo-5-(trifluoromethyl)phenyl)-N-(5-fluorothiazol-2-yl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (0.104 g, 0.194 mmol), and potassium phosphate (0.165 g, 0.776 mmol) in 2 mL dioxane and 1 mL water, was heated to 110° C. 2 hours. The reaction mixture was allowed to cool to room temperature, was diluted with EtOAc and washed with 1N citric acid. The organic layer was then concentrated. Purification of the resulting residue by reverse phase column chromatography [RediSep Gold C18 50 g, 10 to 100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave N-(5-fluorothiazol-2-yl)-5-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-sulfonamide (0.011 g, 0.020 mmol). [M+H]+=553.0 1H NMR (400 mHz, Acetone-d6) δ ppm: 7.70-7.77 (m, 1H), 7.50 (d, J=8.1 Hz, 1H), 7.42 (s, 1H), 7.05-7.14 (m, 2H), 6.93 (d, J=6.7 Hz, 1H), 6.62 (d, J=0.9 Hz, 1H), 5.87-5.93 (m, 1H), 4.48-4.56 (d, J=17.4 Hz, 1H), 4.19 (d, J=17.4 Hz, 1H), 3.70-3.84 (m, 2H), 3.32-3.43 (m, 1H), 3.12-3.32 (m, 3H), 2.87-2.98 (m, 1H), 2.76-2.82 (m, 1H), 2.57 (s, 3H), 1.98-2.04 (m, 2H)
