2-Bromoethanol → HCID 44545940, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-fluoro-5-((5-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)-1H-imidazol-2-yl)methyl)aniline (Example 73) (100 mg, 0.244 mmol) in toluene (450 uL) and DMF (0.2 mL) were added 2-bromoethanol (21 uL, 0.293 mmol), N,N-diisopropylethylamine (300 uL, 1.72 mmol) and the mixture was stirred at 70° C. After 5 hours, additional 2-bromoethanol (5 uL) was added, and stirred at 100° C. for overnight. The reaction mixture was cooled to room temperature, diluted with H2O (4 mL), and extracted with CH2Cl2 (2 mL, 3 times). 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 afford the title compound (38 mg, 34%). 1H NMR (300 MHz, CDCl3) δ 2.49 (3H, s), 3.31 (2H, bs), 3.83 (2H, t), 4.10 (2H, s), 6.56-6.60 (1H, m), 6.76 (1H, d), 6.87-6.96 (2H, m), 7.22 (1H, d), 7.34-7.42 (2H, m), 7.93 (1H, d), 8.09 (1H, d), 8.15 (2H, bs), 8.90 (1H, dd), 10.45 (1H, bs). MS (ESI) m/z 454 (MH+).

Provenance & Evidence