Potassium Carbonate → 6-(2-(4-fluoro-3-(2-(pyrrolidin-1-yl)ethoxy)benzyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)phenol (Example 81) (80 mg, 0.195 mmol) in acetone (6 mL) and DMF (3 mL) were added 1-(2-chloroethyl)pyrrolidine hydrochloride (50 mg, 0.292 mmol) and K2CO3 (81 mg, 0.585 mmol). The mixture was stirred at 60° C. for 6 hours, cooled to room temperature, and diluted with H2O (10 mL). The mixture was extracted with CH2Cl2 (25 mL, 3 times), and then the organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by MPLC on NH silica gel (MeOH:CH2Cl2=1:50 (v/v) to 1:20 (v/v)) to afford the title compound (52.7 mg, 53%). 1H NMR (300 MHz, CDCl3) δ 1.78 (4H, pentet), 2.51 (3H, s), 2.63 (4, td), 2.93 (2H, t), 4.16 (2H, s), 7.18 (2H, t), 6.85-6.90 (1H, m), 6.94-7.07 (3H, m), 7.24 (1H, s), 7.36 (1H, d), 7.41 (1H, dd), 7.97 (1H, dd), 8.09-8.18 (3H, m), 8.92 (1H, dd), 10.01 (1H, bs). MS (ESI) m/z 508 (MH+).

Provenance & Evidence