Ammonium Hydroxide → 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)phenol

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(2-(4-fluoro-3-methoxybenzyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline (Example 80, prepared according to the method described in US 2008/0319012 A1) (948 mg, 2.23 mmol) and pyridine hydrochloride (95 g) was stirred at 190° C. for 80 min. Then the hot reaction mixture was poured into H2O (60 mL) and added NH4OH solution to pH 5. The aqueous solution was extracted with CH2Cl2 (30 mL, 7 times) and then the organic layer was dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified by MPLC (MeOH:CH2Cl2=1:30 (v/v) to 1:15 (v/v)) to afford the solid, which was recrystallized from CH2Cl2/Et2O to give the title compound (635 mg, 69%). 1H NMR (300 MHz, CDCl3) δ 2.34 (3H, s), 3.95 (2H, s), 6.50 (1H, d), 6.56-6.57 (1H, m), 6.79 (1H, dd), 6.91 (1H, d), 7.25-7.33 (2H, m), 7.78 (1H, m), 7.91-7.97 (2H, m), 8.03 (1H, s), 8.81 (1H, d), 10.80 (1H, bs), 11.48 (1H, bs). MS (ESI) m/z 411 (MH+).

Provenance & Evidence