Реакция #46572

Уравнение реакции

3-bromo-5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one

tert-butyl acrylate

DIEA

P(o-tol)3

N2

→

title compound

Выход 58.5%

tert-butyl (E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylate

Выход 58.5%

Растворители

propionitrile

Условия реакции

Обработка

1. 1
   Температураheated
2. 2
   Температураat reflux overnight
3. 3
   ФильтрацияThe dark mixture was filtered through a pad of Celite®
4. 4
   Промывкаthe filter pad was rinsed with acetonitrile (250 mL)
5. 5
   КонцентрированиеThe filtrate was concentrated in vacuo
6. 6
   Другоеthe residue was purified by flash chromatography on silica gel (ethyl acetate)

Методика

A solution of 3-bromo-5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one (1.00 g, 4.15 mmole), tert-butyl acrylate (0.67 mL, 4.60 mmole), DIEA (1.45 mL, 8.30 mmole), Pd(OAc)2 (0.09 g, 0.42 mmole) and P(o-tol)3 (0.25 g, 0.85 mmole) in propionitrile (25 mL) was purged with N2 and then heated at reflux overnight. The dark mixture was filtered through a pad of Celite®, and the filter pad was rinsed with acetonitrile (250 mL). The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (ethyl acetate). The title compound (0.70 g, 58%) was obtained as a light yellow solid after drying in vacuo: MS (ES) m/e 289 (M+H)+.

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