Reaktion #71388

Reaktionsgleichung

5-bromo-8-(3,5-dimethoxy-phenyl)-quinoxalin-2-ol

8-bromo-5-(3,5-dimethoxy-phenyl)-quinoxalin-2-ol

CuCN

→

title compound

8-(3,5-Dimethoxy-phenyl)-2-hydroxy-quinoxaline-5-carbonitrile

Lösungsmittel

EtOAc

ethylenediamine

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to rt
2. 2
   Extraktionextracted with EtOAc
3. 3
   Extraktionextracted with EtOAc
4. 4
   WaschenThe combined organic extracts were washed with H2O and brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (Hex/EtOAc, 7:3)

Vorschrift

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).

Quelle