Phosphorus oxychloride → HCID 59292903, compound

HRID 2409671Notes

Reaction equation

HRID 2409671 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[N:19]=[C:18](O)[CH:17]=[N:16][C:15]=3[C:14]([C:22]#[N:23])=[CH:13][CH:12]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:18]1[CH:17]=[N:16][C:15]2[C:14]([C:22]#[N:23])=[CH:13][CH:12]=[C:11]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)[C:20]=2[N:19]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178493439HCID 178493439, compound

Product 1

HCID 59292903HCID 59292903, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 8-(3,5-dimethoxy-phenyl)-2-hydroxy-quinoxaline-5-carbonitrile (Step 85.5) (100 mg, 0.33 mmol) and POCl3 (1 mL) was stirred at 120° C. for 3 h, allowed to cool to rt and concentrated. The residue was diluted with DCM/NaHCO3 saturated aqueous solution and extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (Hex/EtOAc, 7:3) to afford 90 mg of the title compound as a yellow solid: ES-MS: 326.1 [M+H]+; tR=5.02 min (System 1); Rf=0.34 (Hex/EtOAc, 7:3).

Workup

  1. temperatureto cool to rt
  2. concentrationconcentrated
  3. additionThe residue was diluted with DCM/NaHCO3 saturated aqueous solution
  4. extractionextracted with DCM
  5. washThe organic phase was washed with H2O and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel column chromatography (Hex/EtOAc, 7:3)

Sources & evidence

ORD record
ord-852abf1f06df47e8b714d1dfc391f1e7
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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