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

HRID 2409687Notes

Reaction equation

HRID 2409687 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-97a4f57e27a6408fabba1120425107d6
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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