Sodium Carbonate → HCID 118314210, compound

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 (0.0473 g, 0.104 mmol), (4-((4-chlorobenzyl)oxy)phenyl)boronic acid (0.041 g, 0.156 mmol) and 2M Na2CO3 (0.130 ml, 0.260 mmol) in DMF 92 mL) was degassed for 10 min. Then, Pd(Ph3P)4 (0.012 g, 10.39 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-(5-(4-((4-chlorobenzyl)oxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetate (0.0368 g, 0.062 mmol, 59.7% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.38-7.44 (m, 4H), 7.16-7.19 (m, 1H), 7.02-7.09 (m, 3H), 6.01 (br. s., 1H), 5.09-5.16 (m, 2H), 4.24-4.31 (m, 1H), 4.19 (qd, J=7.1, 10.8 Hz, 1H), 3.04-3.27 (m, 1H), 2.83 (br. s., 1H), 2.67 (br. s., 3H), 2.28 (br. s., 4H), 1.94-2.13 (m, 1H), 1.27 (t, J=7.1 Hz, 3H), 1.20 (s, 9H), 0.88 (m, 3H), 0.68 (br. s., 3H). 4H of piperidine were not resolved. LCMS (M+H)=593.3.

Provenance & Evidence