Potassium Carbonate → 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(1-phenyl-1H-benzo[d]imidazol-6-yl)phenoxy)propan-2-ol

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Reaction Conditions

Reaction Steps

A mixture of 6-bromo-1-phenyl-1H-benzo[d]imidazole (200 mg, 0.73 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 (330 mg, 0.81 mmol), K2CO3 (303 mg, 2.19 mmol) and Pd(dppf)Cl2 (50 mg) in a solution of dioxane (8 mL) and H2O (2 mL) was stirred at 100° C. for 16 h. The catalyst was filtered, and the filtrate concentrated. The residue was purified by prep-HPLC to give the desired title compound (152 mg, 43.8%). 1HNMR(CH3OD, 400 MHz) δ: 8.42 (s, 1H), 8.37 (br, 1H), 8.22-8.20 (m, 1H), 7.70-7.52 (m, 7H), 7.49-7.18 (m, 7H), 6.96-6.93 (m, 1H), 4.53-4.38 (m, 3H), 4.02-3.96 (m, 2H), 3.61-3.55 (m, 2H), 3.48-3.36 (m, 2H), 3.25-3.13 (m, 2H). LCMS (m/z): 476.2 [M+H]+

Provenance & Evidence