Reaction Steps
A mixture of 1-(4-(6-bromo-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)ethanone (56 mg, 0.174 mmol), 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)propan-2-ol (71 mg, 0.174 mmol), Pd(dppf)Cl2 (13 mg, 0.018 mmol) and K2CO3 (72 mg, 0.521 mmol) in H2O-dioxane (11 mL/3 mL) was stirred at 100° C. under microwave heating for 15 min. The reaction mixture was then concentrated and the residue purified by HPLC separation to yield the desired title compound as a formate salt (12.4 mg, yield: 13.6%). 1H NMR (400 MHz, MeOD): 8.41 (brs, 1H), 8.36 (s, 1H), 7.89 (s, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.59 (d, J=1.2 Hz, 1H), 7.58 (d, J=1.6 Hz, 1H), 7.42 (t, J=8 Hz, 1H), 7.40-7.25 (m, 5H), 7.20 (d, J=6.8 Hz, 1H), 7.00 (dd, J=1.6, 8 Hz, 1H), 4.84-4.78 (m, 2H), 4.50 (dd, J=4.0, 9.2 Hz, 1H), 4.38 (s, 2H), 4.17 (d, J=4.8 Hz, 3H), 3.53-3.50 (m, 2H), 3.46-3.33 (m, 3H), 3.18 (s, 2H), 2.94-2.88 (m, 1H), 2.31-2.25 (m, 2H), 2.21 (s, 3H), 2.19-2.10 (m, 1H), 2.03 (dd, J=4.4, 12.0 Hz, 1H) ppm; ESI-MS (m/z): 300.1 [M+1]+.
