5-Bromo-8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline → 8-(2-Fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrile

HRID 1189810Notes

Reaction equation

HRID 1189810 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])[C:13]=2[F:22])=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2.[C:23]([Cu])#[N:24]>CN1C(=O)CCC1.C(Cl)Cl>[F:22][C:13]1[C:14]([O:20][CH3:21])=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=1[C:9]1[C:8]2[N:7]=[CH:6][CH:5]=[N:4][C:3]=2[C:2]([C:23]#[N:24])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 592929615-Bromo-8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxalineHCID 178418546HCID 178418546, compound

Product 1

HCID 592929178-(2-Fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrileYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-bromo-8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline (Step 94.3) (3.09 g, 8.5 mmol) and CuCN (918 mg, 10.2 mmol, 1.2 equiv) in NMP (30 mL) was stirred for 6.5 h at 160° C., under an argon atmosphere. The reaction mixture was allowed to cool to rt, diluted with DCM/(10% aqueous solution of ethylenediamine) (200 mL, v/v 1:1), filtered through celite and the filtrate extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was triturated in DCM to provide 1.63 g of the title compound as a white solid: ESI-MS: 310.1 [M+H]+; tR=4.41 min (System 1).

Workup

  1. temperatureto cool to rt
  2. filtrationfiltered through celite
  3. extractionthe filtrate extracted with DCM
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated in DCM

Sources & evidence

ORD record
ord-96e20713a321408f9e748af8eee4b320
Source dataset
uspto-grants-2014_03
Patent number
US08674099B2

Reaction notes

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