Sodium Carbonate → (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate

Participants

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 (0.0454 g, 0.100 mmol), (4-((4-methoxybenzyl)oxy)phenyl)boronic acid (0.039 g, 0.150 mmol) and 2M Na2CO3 (0.125 ml, 0.249 mmol) in DMF 92 mL) was degassed for 10 min. Then, Pd(Ph3P)4 (0.012 g, 9.97 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-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (0.0376 g, 0.064 mmol, 64.1% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.40-7.44 (m, 2H), 7.15-7.18 (m, 1H), 7.04-7.09 (m, 3H), 6.94-6.98 (m, 2H), 6.05 (br. s., 1H), 5.05-5.11 (m, 2H), 4.27 (qd, J=7.1, 10.8 Hz, 1H), 4.18 (qd, J=7.1, 10.7 Hz, 1H), 3.86 (s, 3H), 3.19 (br. s., 1H), 2.87 (br. s., 1H), 2.63 (br. s., 3H), 2.24 (br. s., 4H), 2.05 (br.s., 1H), 1.26 (t, J=7.1 Hz, 3H), 1.20 (s, 9H), 0.90 (m, 3H), 0.66 (br. s., 3H). 4H of piperidine were not resolved. LCMS (M+H)=589.4.

Provenance & Evidence