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

HRID 2409779Notes

Reaction equation

HRID 2409779 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 179.4) (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 [M+H]+; tR=4.53 min (System 1).

Workup

  1. temperatureto cool to rt
  2. filtrationfiltered

Sources & evidence

ORD record
ord-1341a54d2d744e0396032b2399b10f3e
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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