Dimethylformamide → 2-((5-Chloro-3-(3-fluorophenyl)-quinoxalin-2-yl)methyl)isoindoline-1,3-dione
Reaction equation
Br[CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:20])[N:4]=1.CN(C=O)C.[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.[K]>>[Cl:20][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:11]=[C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[C:3]([CH2:2][N:30]1[C:26](=[O:36])[C:27]3[C:28](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:29]1=[O:31])=[N:4]2Participants
Conditions
- Temperature
- 100 °C
Procedure
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 2-((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.
Workup
- stirringAfter stirring at 100° C. for 1 h
- concentrationthe mixture was concentrated under reduced pressure
- customtriturated with water (30 mL)
- filtrationThe precipitate was collected by filtration
- washThe solid was washed with water (50 mL)
- dry with materialMeOH (100 mL), and dried
Sources & evidence
- ORD record
- ord-58b66cc19ec64b35bee4f711d5f4431b
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586739B2
Reaction notes
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