5-Bromo-8-(3,5-dimethoxy-phenyl)-quinoxaline → 8-(3,5-Dimethoxy-phenyl)-quinoxaline-5-carbonitrile

HRID 2391759Notes

Reaction equation

HRID 2391759 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=2)=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2.[C:22]([Cu])#[N:23]>CN1C(=O)CCC1.CCOC(C)=O>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([C:9]2[C:8]3[N:7]=[CH:6][CH:5]=[N:4][C:3]=3[C:2]([C:22]#[N:23])=[CH:11][CH:10]=2)[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=1

Participants

5

Reactant 2

HCID 592928255-Bromo-8-(3,5-dimethoxy-phenyl)-quinoxalineHCID 178418546HCID 178418546, compound

Product 1

HCID 592928848-(3,5-Dimethoxy-phenyl)-quinoxaline-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 5-bromo-8-(3,5-dimethoxy-phenyl)-quinoxaline (Step 1.4) (4.54 g, 13.2 mmol) and CuCN (1.54 g, 17.1 mmol, 1.3 equiv) in NMP (50 mL) was stirred for 2 h at 180° C., under an argon atmosphere. The reaction mixture was allowed to cool to rt, diluted with EtOAc (10% aqueous solution of ethylenediamine) (150 mL), and filtered to afford 1.19 g (batch 1) of the title compound as a yellow solid. The filtrate was extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was triturated in EtOAc to provide 2.31 g (batch 2) of the title compound: ESI-MS: 292.1 [M+H]+; tR=4.53 min (System 1).

Workup

  1. temperatureto cool to rt
  2. filtrationfiltered

Sources & evidence

ORD record
ord-6816b965a9ec4df5a269e9fbf1e39475
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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