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 (0.0462 g, 0.101 mmol), (4-phenoxyphenyl)boronic acid (0.033 g, 0.152 mmol) and 2M Na2CO3 (0.127 ml, 0.254 mmol) degassed for 10 min. Then, Pd(Ph3P)4 (0.012 g, 10.14 μmol) added, degassed for 5 min and placed in a pre-heated oil bath 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)-2,6-dimethyl-5-(4-phenoxyphenyl)pyridin-3-yl)acetate (0.0162 g, 0.030 mmol, 29.3% yield) as white solid. 1H NMR (500 MHz, CDCl3 δ7.34-7.39 (m, 2H), 7.24-7.28 (m, 1H), 7.09-7.17 (m, 4H), 7.04-7.08 (m, 2H), 6.09 (s, 1H), 4.14-4.30 (m, 2H), 3.20 (d, J=12.3 Hz, 1H), 2.88 (t, J=11.7 Hz, 1H), 2.62 (s, 3H), 2.33 (d, J=11.5 Hz, 1H), 2.25 (s, 3H), 2.12 (t, J=11.4 Hz, 1H), 1.57 (dt, J=4.3, 12.5 Hz, 1H), 1.37-1.44 (m, 1H), 1.26 (t, J=7.1 Hz, 4H), 1.19-124 (m, 1H), 1.22 (s, 9H), 1.12 (d, J=12.1 Hz, 1H), 0.93 (s, 3H), 0.72 (s, 3H). LCMS (M+H)=545.4.
