HCID 178418546, compound → HCID 178493439, compound

HRID 43110Notes

Reaction equation

HRID 43110 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][C:6]([OH:22])=[N:7]2.BrC1C=CC(C2C=C(OC)C=C(OC)C=2)=[C:28]2C=1N=C(O)C=[N:29]2.C([Cu])#N>CN1C(=O)CCC1.CCOC(C)=O.C(N)CN>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([C:9]2[C:8]3[N:7]=[C:6]([OH:22])[CH:5]=[N:4][C:3]=3[C:2]([C:28]#[N:29])=[CH:11][CH:10]=2)[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=1

Participants

7

Reactant 3

HCID 178418546HCID 178418546, compoundHCID 178493437HCID 178493437, compoundHCID 178493438HCID 178493438, compound

Product 1

HCID 178493439HCID 178493439, compound

Reagents, catalysts & solvents 3

HCID 3301EthylenediamineSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 5-bromo-8-(3,5-dimethoxy-phenyl)-quinoxalin-2-ol and 8-bromo-5-(3,5-dimethoxy-phenyl)-quinoxalin-2-ol (Step 85.6) (609 mg, 1.7 mmol) (Step 1.4) and CuCN (183 mg, 2.0 mmol, 1.2 equiv) in NMP (5 mL) was stirred at 180° C. for 2 h. The reaction mixture was allowed to cool to rt, diluted with EtOAc/10% aqueous solution of ethylenediamine (25 mL) and extracted with EtOAc. The aqueous phase was acidified to pH 5 and extracted with EtOAc. The combined organic extracts were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 7:3) to afford 103 mg of the title compound as a yellow solid: ES-MS: 308.1 [M+H]+; tR=4.05 min (System 1); Rf=0.35 (Hex/EtOAc, 7:3).

Workup

  1. temperatureto cool to rt
  2. extractionextracted with EtOAc
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 7:3)

Sources & evidence

ORD record
ord-e94de5ab86d24720a730dd42f7d54c7e
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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