Réaction #73969

Équation de réaction

(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

Rendement 47.1%

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

Rendement 47.1%

Solvants

DCM

DCM

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source