Potassium Carbonate → 2-(4-isopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(5-propylpyridin-2-yl)methyl]acetamide

Participants

Reaction Steps

N-[(S)-(5-bromopyridin-2-yl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-isopropylphenyl)acetamide (0.075 g, 0.18 mmol) was mixed with n-propylboronic acid (0.04 g, 0.44 mmol), PdCl2(dppf)2 (0.014 g, 0.019 mmol), Ag2O (0.10 g, 0.44 mmol) and K2CO3 (0.073 g, 0.53 mmol) and degassed. THF (3 mL) was added and the mixture was heated in microwave at 130 C for 30 min. The reaction mixture was diluted with EtOAc and filtered through Celite. The solvent was removed and the residue was purified by reverse HPLC to give 2-(4-isopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(5-propylpyridin-2-yl)methyl]acetamide (0.035 g, 51%). ES-MS [M+1]+: 430.1. 1H NMR (CDCl3, 400 MHz) δ 1H NMR (CDCl3, 400 MHz) δ 8.29 (d, J=2.0 Hz, 1H), 7.58 (d, J=6.4 Hz, 1H), 7.45 (dd, J=2.4, 8.0 Hz, 1H), 7.40 (s, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.24-7.19 (ABq, 4H), 6.27 (d, J=7.2 Hz, 1H), 3.98 (s, 3H), 3.62 (s, 2H), 2.94-2.85 (m, J=6.8 Hz, 1H), 2.54 (t, J=7.6 Hz, 2 H), 1.66-1.56 (m, 2H), 1.24 (d, J=6.4 Hz, 6H), 0.93 (t, J=7.2 Hz, 3H). HRMS (ES) [M+1]+ calcd for C23H29N5O: 392.2445. Found: 392.2446.

Provenance & Evidence