Реакция #73969

Уравнение реакции

(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

Выход 47.1%

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

Выход 47.1%

Растворители

DCM

DCM

Условия реакции

Обработка

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

Методика

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).

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