Reaction Steps
A mixture of (S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.514 g, 1.129 mmol), (4-(benzyloxy)phenyl)boronic acid (0.515 g, 2.257 mmol) and 2M Na2CO3 (1.693 ml, 3.39 mmol) in DMF (10 mL) was degassed for 10 min. Then, Pd(Ph3P)4 (0.065 g, 0.056 mmol) was added, degassed for 5 min and placed in a pre-heated oil bath at 110° C. After 2 h, cooled, diluted with ether (50 mL), washed with water (4×10 mL), brine (10 mL), dried (MgSO4), filtered, concentrated and purified by flash chromatography using 10, 20 and 30% EtOAc/Hex to afford (S)-ethyl 2-(5-(4-(benzyloxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.4345 g, 0.778 mmol, 68.9% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.48-7.51 (m, 2H), 7.40-7.45 (m, 2H), 7.34-7.38 (m, 1H), 7.16-7.20 (m, 1H), 7.04-7.10 (m, 3H), 6.09 (s, 1H), 5.13-5.20 (m, 2H), 4.26 (qd, J=7.1, 10.7 Hz, 1H), 4.17 (qd, J=7.1, 10.7 Hz, 1H), 3.18 (d, J=11.8 Hz, 1H), 2.87 (t, J=11.8 Hz, 1H), 2.27 (d, J=11.8 Hz, 1H), 2.21 (s, 3H), 2.05 (t, J=11.7 Hz, 1H), 1.56 (dt, J=4.6, 12.9 Hz, 2H), 1.32-1.41 (m, 1H), 1.26 (t, J=7.1 Hz, 3H), 1.21 (s, 9H), 1.18 (br. s., 1H), 1.05-1.11 (m, 1H), 0.91 (s, 3H), 0.64 (s, 3H). LCMS (M+H) 559.5.
