Dimethylformamide → 2-((5-Chloro-3-(3-fluorophenyl)-quinoxalin-2-yl)methyl)isoindoline-1,3-dione

HRID 216866Notes

Reaction equation

HRID 216866 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]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24194345Phthalimide potassium saltHCID 577078502-(Bromomethyl)-5-chloro-3-(3-fluorophenyl)quinoxaline

Product 1

HCID 577078432-((5-Chloro-3-(3-fluorophenyl)-quinoxalin-2-yl)methyl)isoindoline-1,3-dione

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 (1H, dd, J=7.6, 1.4 Hz), 7.84-7.92 (5H, m), 7.60-7.81 (4H, m), 7.38-7.46 (1H, m), 5.22 (2H, s); LC-MS (ESI) m/z 418.1 [M+H]+. The crude product was carried on crude without purification for the next step.

Workup

  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

Sources & evidence

ORD record
ord-a2235729544e4c2cbdd16311987e351f
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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