Reacción #1591676

Ecuación de reacción

(E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-chloro-2-methoxyphenyl)amino)phenyl)acrylate

Sodium methoxide

→

6-(benzylthio)-1-(4-bromo-5-chloro-2-methoxyphenyl)quinolin-2(1H)-one

Rendimiento 75.2%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto give a yellow suspension
2. 2
   Otroa reflux condenser was attached
3. 3
   Otrowas lowered into a 70° C.
4. 4
   Temperaturaheating bath
5. 5
   TemperaturaThe mixture was cooled to rt
6. 6
   workup.ADDITIONpoured through a 3 inch silica plug
7. 7
   Otroto remove black particulates
8. 8
   Lavadowas washed through the plug with DCM
9. 9
   ConcentraciónThe mother liquor was concentrated to half its volume
10. 10
    workup.ADDITIONIPA (500 mL) was added
11. 11
    Concentraciónthe solution concentrated again
12. 12
    workup.ADDITIONAn additional 500 mL of IPA was added
13. 13
    Otroa tan solid precipitated
14. 14
    FiltraciónThe tan solid was collected by vacuum filtration

Procedimiento

A flask was charged with (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-chloro-2-methoxyphenyl)amino)phenyl)acrylate (73.2 g, 137 mmol) and MeOH (687 ml) to give a yellow suspension. Sodium methoxide (25 wt % in MeOH) (15.01 ml, 54.9 mmol) was added and a reflux condenser was attached. The flask was lowered into a 70° C. heating bath and stirred at 70° C. for 18 h. The mixture was cooled to rt and poured through a 3 inch silica plug to remove black particulates. The product that was crashed out on the silica plug was washed through the plug with DCM. The mother liquor was concentrated to half its volume, then IPA (500 mL) was added and the solution concentrated again. An additional 500 mL of IPA was added and a tan solid precipitated. The tan solid was collected by vacuum filtration to give 6-(benzylthio)-1-(4-bromo-5-chloro-2-methoxyphenyl)quinolin-2(1H)-one (50.34 g, 103 mmol, 75% yield) as a dark tan powdery solid. m/z (ESI) 486.0 (M+H)+.

Fuente