Reacción #73969

Ecuación de reacción

(E)-ethyl 3-(4-(4-(chlorosulfonyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate

intermediate 41.3

(E)-ethyl 3-(4-(4-(chlorosulfonyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate

2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethanamine

triethylamine

water

→

title compound

Rendimiento 47.1%

(E)-ethyl 3-(4-(4-(N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)sulfamoyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate

Rendimiento 47.1%

Disolventes

DCM

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe reaction mixture was extracted with DCM (2×25 mL)
2. 2
   LavadoThe combined orgaic layers were washed with water (10 mL), brine (10 mL)
3. 3
   Secadodried (Na2SO4)
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe crude material was purified by flash chromatography on silica gel eluting with 50% EtOAc in DCM

Procedimiento

To a solution of (E)-ethyl 3-(4-(4-(chlorosulfonyl)phenoxy)-3,5-difluorophenyl)-2-methylacrylate (intermediate 41.3) (250 mg, 0.60 mmol) in DCM (3 mL) was added a solution of 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethanamine (157 mg, 0.72 mmol) and triethylamine (72 mg, 0.72 mmol) in DCM (2 mL). After 15 minutes, water (10 mL) was added and the reaction mixture was extracted with DCM (2×25 mL). The combined orgaic layers were washed with water (10 mL), brine (10 mL), dried (Na2SO4) and concentrated. The crude material was purified by flash chromatography on silica gel eluting with 50% EtOAc in DCM to give the title compound (169 mg).

Fuente