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 (0.0433 g, 0.095 mmol), (4-((2-methoxybenzyl)oxy)phenyl)boronic acid (0.037 g, 0.143 mmol) and 2M Na2CO3 (0.119 ml, 0.238 mmol) in DMF (2 mL) was degassed for 10 min. Then, Pd(Ph3P)4 (10.99 mg, 9.51 μmol) was added, degassed for 5 min and placed in a oil bath pre-heated to 110° C. After 2 h, cooled and purified by pre-HPLC to afford (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-((2-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (0.038 g, 0.065 mmol, 67.9% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.51 (dd, J=1.6, 7.4 Hz, 1H), 7.34 (dt, J=1.7, 7.8 Hz, 1H), 7.15-7.18 (m, 1H), 7.04-7.10 (m, 3H), 7.01 (dt, J=0.9, 7.5 Hz, 1H), 6.96 (d, J=8.2 Hz, 1H), 6.03 (br. s., 1H), 5.17-5.25 (m, 2H), 4.23-4.31 (m, 1H), 4.19 (qd, J=7.1, 10.7 Hz, 1H), 3.91 (s, 3H), 3.05-3.28 (m, 1H), 2.87 (br. s., 1H), 2.66 (br. s., 3H), 2.28 (br. s., 3H), 1.95-2.15 (m, 1H), 1.27 (t, J=7.1 Hz, 3H), 1.20 (s, 9H), 0.9 (br.s., 3H), 0.68 (br. s., 3H). 5H of piperidine were not resolved. LCMS (M+H)=589.4.
