Phthalimide → 2-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl)isoindoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

In a 250 mL flask, 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-ol (3.00 g, 8.24 mmol), phthalimide (2.50 g, 17.3 mmol) and triphenylphosphine (5.20 g, 19.8 mmol) were diluted with tetrahydrofuran (30 mL). The reaction mixture was cooled to 0° C. and diisopropylazodicarboxylate (4.00 g, 19.8 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated and loaded onto silica gel. The resulting slurry was purified by flash column chromatography using 10% ethyl acetate/petroleum ether as eluent to afford the title compound as white solid (2.50 g, 75%); mp 114-118° C.; 1H NMR (300 MHz, CDCl3) δ 8.53 (s, 1H), 8.07 (d, J=8.1 Hz, 2H), 7.86-7.76 (m, 4H), 7.72-7.66 (m, 2H), 7.37 (d, J=8.7 Hz, 2H), 7.31 (d, J=7.5 Hz, 2H), 3.77 (t, J=6.9 Hz, 2H), 2.75 (t, J=7.8 Hz, 2H), 2.08 (t, J=6.9 Hz, 2H); ES+API m/z 493 ([M+H]+).

Provenance & Evidence