Nitrogen → 3-Cyclobutyl-1-(2-pyridin-4-ylquinolin-7-yl)imidazo[1,5-a]pyrazin-8-ylamine

Participants

Reaction Conditions

Reaction Steps

N2 was bubbled into a stirred mixture of 1-bromo-3-cyclobutylimidazo[1,5-a]pyrazin-8-ylamine (48 mg, 0.18 mmol), 2-pyridin-4-yl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)quinoline (90 mg, 0.27 mmol), Pd(PPh3)4 (12.5 mg, 0.0108 mmol), and Na2CO3 (48 mg, 0.45 mmol) in DMF/H2O (5/1, 6 mL) for 5 min. This mixture was then stirred at 80° C. under N2 for 40 h. The solvents were removed; the residue was dissolved in MeOH and submitted to the mass-directed purification system and provided the desired product; 1H-NMR (CDCl3, 400 MHz) δ 2.02-2.10 (m, 1 H), 2.17-2.24 (m, 1 H), 2.50-2.57 (m, 2 H), 2.62-2.70 (m, 2 H), 3.84-3.89 (m, 1 H), 5.45 (s, br, 2 H), 7.10 (d, J=4.4 Hz, 1 H), 7.17 (d, J=5.2 Hz, 1 H), 7.96 (d, J=8.8 Hz, 1 H), 8.00-8.01 (m, 2 H), 8.10 (d, J=6.0 Hz, 2 H), 8.35 (d, J=8.4 Hz, 1 H), 8.45 (s, 1 H), 8.80 (d, J=4.8 Hz, 2 H); MS (ES+): m/z 393 [MH+]; HPLC: tR=1.94 min (OpenLynx, polar—5 min).

Provenance & Evidence