HCID 66914543, compound → HCID 66914516, compound

HRID 1189816Notes

Reaction equation

HRID 1189816 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([CH3:19])=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=2)=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2.[C:20]([Cu])#[N:21]>CN1C(=O)CCC1.C(Cl)Cl.C(N)CN>[CH3:19][C:13]1[C:12]([C:9]2[C:8]3[N:7]=[CH:6][CH:5]=[N:4][C:3]=3[C:2]([C:20]#[N:21])=[CH:11][CH:10]=2)=[CH:17][C:16]([CH3:18])=[CH:15][N:14]=1

Participants

6

Reactant 2

HCID 66914543HCID 66914543, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 66914516HCID 66914516, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 3301EthylenediamineSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-bromo-8-(2,5-dimethyl-pyridin-3-yl)-quinoxaline (Step 99.4) (189 mg, 0.60 mmol) and CuCN (70 mg, 0.78 mmol, 1.3 equiv) in NMP (2 mL) was stirred for 6 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 (25 mL), extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) to afford 150 mg of the title compound as a yellow solid. Title compound: ESI-MS: 261.2 [M+H]+; tR=1.92 min (System 1); TLC: Rf=0.68 (DCM/MeOH/NH3aq, 94:5:1).

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 purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Sources & evidence

ORD record
ord-5e52624d048b42e586e6b70781919c82
Source dataset
uspto-grants-2014_03
Patent number
US08674099B2

Reaction notes

Loading…