Реакция #676080

Уравнение реакции

1-chloro-2-cyclopropyl-4-iodo-5-methoxybenzene

tert-butyl 3-(4-acryloylpiperazin-1-yl)azetidine-1-carboxylate

sodium acetate

→

desired product

Выход 84.0%

(E)-1-(4-(1-Acryloylazetidin-3-yl)piperazin-1-yl)-3-(4-chloro-5-cyclopropyl-2-methoxyphenyl)prop-2-en-1-one

Выход 84.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was partitioned between ethyl acetate and water
2. 2
   ПромывкаThe organic layer was washed with brine
3. 3
   Сушкаdried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   Другоеto purified by silica gel (dichloromethane/methanol=40:1)

Методика

A mixture of 1-chloro-2-cyclopropyl-4-iodo-5-methoxybenzene (300 mg, 0.974 mmol), tert-butyl 3-(4-acryloylpiperazin-1-yl)azetidine-1-carboxylate (431 mg, 1.46 mmol), Pd(OAc)2 (54.6 mg, 0.243 mmol), sodium acetate (239 mg, 2.92 mmol), tetrabutylammonium chloride (539 mg, 1.95 mmol) in DMF (7 mL) was stirred at 100° C. for 24 h. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to purified by silica gel (dichloromethane/methanol=40:1) to afford the desired product (350 mg, 84% yield). ESI-MS m/z: 476.2[M+H]+.

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