Reaction #73969

Reaction equation

(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

Yield 47.1%

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

Yield 47.1%

Solvents

DCM

DCM

Conditions

Workup

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

Procedure

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