HCID 59292933, compound → 8-(2,6-Difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrile

HRID 43115Notes

Reaction equation

HRID 43115 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([F:18])=[C:16]([O:19][CH3:20])[CH:15]=[C:14]([O:21][CH3:22])[C:13]=2[F:23])=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2.[C:24]([Cu])#[N:25]>CN1C(=O)CCC1.C(Cl)Cl>[F:23][C:13]1[C:14]([O:21][CH3:22])=[CH:15][C:16]([O:19][CH3:20])=[C:17]([F:18])[C:12]=1[C:9]1[C:8]2[N:7]=[CH:6][CH:5]=[N:4][C:3]=2[C:2]([C:24]#[N:25])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 59292933HCID 59292933, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 592928748-(2,6-Difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carbonitrileYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-bromo-8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline (Step 88.3) (1.1 g, 2.9 mmol) (Step 88.3) and CuCN (312 mg, 3.4 mmol, 1.2 equiv) in NMP (10 mL) was stirred for 4 h at 150° C., under an argon atmosphere. The reaction mixture was allowed to cool to rt, diluted with DCM/(10% aqueous solution of ethylenediamine) (100 mL) and 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 702 mg of the title compound as a beige solid: ESI-MS: 328.1 [M+H]+; tR=4.48 min (System 1).

Workup

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

Sources & evidence

ORD record
ord-e2402069c5b34033a64688f9b568f245
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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