Phosphorus oxychloride → 4-(4-Chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole
Reaktionsgleichung
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11](=O)[C:12]([N+:17]([O-:19])=[O:18])=[CH:13][NH:14]3)=[CH:9][C:8]=2[O:21][CH3:22])=[C:5]([CH3:23])[O:4][N:3]=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:11]1[C:10]2[C:15](=[CH:16][C:7]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:23])=[C:8]([O:21][CH3:22])[CH:9]=2)[N:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]Komponenten
3
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-3-nitroquinolin-4(1H)-one (for a preparation see Intermediate 6) (4.78 g, 15.16 mmol) was dissolved in POCl3 (10 ml, 107 mmol) and the mixture was heated at 110° C. for 3 h, then cooled and evaporated in vacuo, The residue was suspended in toluene (20 ml) and evaporated in vacuo, then the residue was suspended in DCM (100 ml) and saturated sodium hydrogen carbonate solution (100 ml) and stirred for 10 min. The organic layer was dried and evaporated and the residue dissolved in DCM (10 ml) and loaded onto a 100 g silica column, then eluted with 0-60% EtOAc/cyclohexane to give 4-(4-chloro-6-methoxy-3-nitroquinolin-7-yl)-3,5-dimethylisoxazole (3.21 g, 9.62 mmol, 63.4% yield) as a bright yellow powder. LCMS (formate) Rt 1.13 min, MH+ 334