Phthalimide → 2-(1-(5-Chloro-3-(3-fluorophenyl)quinoxalin-2-yl)ethyl)isoindoline-1,3-dione

Participants

Reaction Steps

To a solution of 1-(5-chloro-3-(3-fluorophenyl)quinoxalin-2-yl)ethanol (0.2875 g, 0.9497 mmol) in tetrahydrofuran (9.497 mL, 0.9497 mmol) were added triphenyl-phosphine (0.7473 g, 2.849 mmol), phthalimide (0.4192 g, 2.849 mmol), and diisopropyl azodicarboxylate (0.5518 mL, 2.849 mmol). The reaction mixture was stirred at room temperature. After 1 h, the mixture was concentrated under reduced pressure and partitioned between EtOAc (100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on a 40 g of Redi-Sep™ column using 0 to 50% gradient of EtOAc in hexane over 20 min and 50% isocratic of EtOAc for 5 min as eluent to give 2-(1-(5-chloro-3-(3-fluorophenyl)quinoxalin-2-yl)ethyl)isoindoline-1,3-dione as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.19 (1H, dd, J=8.4, 1.4 Hz), 8.09 (1H, dd, J=7.6, 1.4 Hz), 7.91 (1H, dd, J=8.4, 7.6 Hz), 7.73-7.80 (2H, m), 7.60-7.68 (2H, m), 7.31-7.38 (1H, m), 7.14-7.24 (2H, m), 7.00-7.09 (1H, m), 6.04-6.13 (1H, m), 1.77 (3H., d, J=6.7 Hz); LC-MS (ESI) m/z 432.1 [M+H]+.

Provenance & Evidence