Sodium Hydroxide → HCID 178424679, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)benzonitrile (Example 76) (100 mg, 0.238 mmol) and sodium azide (20.9 mg, 0.321 mmol) in toluene (1 mL) was stirred at 120° C. for overnight. The reaction mixture was cooled to room temperature and basified to pH 9-10 with 5N NaOH solution in the ice bath. The mixture was extracted with CH2Cl2 (5 mL, 3 times), and then the aqueous layer was acidified to pH 4 with 2N HCl solution. The precipitate was filtered, washed with H2O, and dried under vacuum for overnight to afford the solid, which was recrystallized from MeOH/CH2Cl2/Et2O to give the title compound (56 mg, 51%). (300 MHz, CDCl3+CD3OD) δ 2.49 (3H, s), 4.17 (2H, s), 6.98 (1H, d), 7.08 (1H, dd), 7.13 (1H, d), 7.35-7.41 (2H, m), 7.45-7.50 (1H, m), 7.81 (1H, dd), 7.97-8.01 (2H, m), 8.05 (1H, d), 8.13 (1H, dd), 8.80 (1H, dd). MS (ESI) m/z 463 (MH+).

Provenance & Evidence