Reaction Steps
To a degassed solution of 6-bromo-2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole (190 mg, 0.438 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (163 mg, 0.526 mmol) and K2CO3 (182 mg, 1.315 mmol) in dioxane (3 mL) and water (1 mL) was added Pd(Ph3P)4 (25.3 mg, 0.022 mmol). Upon completion of addition, the reaction mixture was heated to 100° C., where it stirred overnight. At the conclusion of this period, the reaction mixture was cooled to rt, diluted with water and then extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated to yield a residue. The residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 50% EtOAc) to afford Compound 1D as a white solid (166 mg, 0.310 mmol, 71% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 8.17 (2H, s), 7.62-7.65 (1H, m), 7.62 (1H, s), 7.40 (1H, dd, J=8.5, 1.9 Hz), 6.00-6.09 (1H, m), 5.42-5.49 (1H, m), 4.23 (2H, ddd, J=13.3, 6.7, 3.9 Hz), 4.05-4.13 (2H, m), 3.63-3.76 (4H, m), 2.53-2.61 (2H, m), 2.41 (2H, t, J=7.6 Hz), 2.14-2.23 (2H, m), 1.95 (2H, dddd, J=12.8, 8.5, 8.4, 3.9 Hz), 1.57-1.64 (2H, m), 1.51 (9H, s), 0.95 (3H, t, J=7.3 Hz).
