2-Chloroquinoxaline → HCID 18689870, compound

HRID 1871919Notes

Reaction equation

HRID 1871919 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.FC(F)(F)S(O[C:18]1[CH2:24][CH:23]2[N:25]([CH3:26])[CH:20]([CH2:21][CH2:22]2)[CH:19]=1)(=O)=O.C[Sn](C)C.C[Sn](C)C.[Cl-].[Li+].[F-].[K+]>O1CCOCC1.C(OCC)(=O)C>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:10]=[CH:11][C:2]=1[C:18]1[CH2:19][CH:20]2[N:25]([CH3:26])[CH:23]([CH2:22][CH2:21]2)[CH:24]=1

Participants

8

Reactant 5

HCID 2389382-ChloroquinoxalineHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 6327618HexamethylditinHCID 11993054(-)-8-methyl-3-(trifluoromethylsulfonyloxy)-8-aza-bicyclo[3.2.1]oct-2-ene

Product 1

HCID 18689870HCID 18689870, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloroquinoxaline, 3-trifluoromethanesulfonyloxy-8-methyl-8-azabicyclo[3.2.1]-oct-2-ene, hexamethylditin, lithium chloride, and [tetrakis(triphenylphosphine)]palladium in dioxane is stirred at reflux for 18 hours. The reaction mixture is cooled to room temperature and then poured into a mixture of saturated aqueous potassium fluoride and ethyl acetate. After stirring for two hours, the phases are separated. The organic phase is washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue is subjected to flash silica gel chromatography. Fractions containing product are combined and concentrated under reduced pressure to provide the title compound.

Workup

  1. temperatureat reflux for 18 hours
  2. stirringAfter stirring for two hours
  3. customthe phases are separated
  4. washThe organic phase is washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b592d0cdb814aa581c5c245ff306898
Source dataset
uspto-grants-2000_08
Patent number
US06107307

Reaction notes

Loading…