Dimethylformamide → Phthalimide

Temperature

100 °C

To a heterogeneous mixture of 2-(bromomethyl)-5-chloro-3-(3-fluorophenyl)-quinoxaline (0.2401 g, 0.6829 mmol) in DMF (5.003 mL, 0.6829 mmol) was added potassium phthalimide (0.3162 g, 1.707 mmol) and the heterogeneous mixture was stirred at 100° C. After stirring at 100° C. for 1 h, the mixture was concentrated under reduced pressure and triturated with water (30 mL). The precipitate was collected by filtration. The solid was washed with water (50 mL), then MeOH (100 mL), and dried to give 24(5-chloro-3-(3-fluorophenyl)-quinoxalin-2-yl)methyl)isoindoline-1,3-dione as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.04 (1 H, dd, J=7.6, 1.4 Hz), 7.84-7.92 (5 H, m), 7.60-7.81 (4 H, m), 7.38-7.46 (1 H, m), 5.22 (2 H, s); LC-MS (ESI) m/z 418.1 [M+H]+. The crude product was carried on crude without purification for the next step.

1. stirringAfter stirring at 100° C. for 1 h
2. concentrationthe mixture was concentrated under reduced pressure
3. customtriturated with water (30 mL)
4. filtrationThe precipitate was collected by filtration
5. washThe solid was washed with water (50 mL)
6. dry with materialMeOH (100 mL), and dried

ORD record

ord-577cef92dbb0469fa4e982ef6a93b5b7

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901135B2