Reaction Steps
To a degassed solution of 6-bromo-2-((1-(5-propylpyrimidin-2-yl)piperidin-4-yl)methyl)benzo[d]oxazole (0.15 g, 0.361 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.156 g, 0.506 mmol) and K2CO3 (0.125 g, 0.903 mmol) in dioxane (3.7 mL) and water (1.2 mL) was added Pd(Ph3P)4 (0.021 g, 0.018 mmol). The reaction mixture was stirred at 100° C. for 15 h. The reaction mixture was cooled to rt, and diluted with EtOAc/Ether (10 mL, 1:1 v/v). The organic layer was washed with NaHCO3 (aq, sat, 6 mL) and NaCl (saturated aqueous, 6 mL). It was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 60% EtOAc) to afford desired product as a light yellow solid (180 mg, 96% yield). 1H NMR (400 MHz, chloroform-d) δ 8.14 (s, 2H), 7.61 (d, J=8.3 Hz, 1H), 7.47 (d, J=1.3 Hz, 1H), 7.38-7.33 (m, 1H), 6.15-5.95 (m, 2H), 4.73 (d, J=13.4 Hz, 1H), 4.10 (s, 2H), 3.67 (t, J=5.6 Hz, 3H), 2.99-2.79 (m, 3H), 2.57 (s, 2H), 2.46-2.33 (m, 2H), 2.32-2.13 (m, 2H), 1.87 (d, J=11.2 Hz, 2H), 1.63-1.53 (m, 1H), 1.50 (s, 9H), 1.37 (dd, J=12.5, 4.0 Hz, 2H), 0.93 (t, J=7.3 Hz, 3H). LCMS (m/z)=518 (M+H)+.
