Reacción #46572

Ecuación de reacción

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

Rendimiento 58.5%

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

Rendimiento 58.5%

Disolventes

propionitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaat reflux overnight
3. 3
   FiltraciónThe dark mixture was filtered through a pad of Celite®
4. 4
   Lavadothe filter pad was rinsed with acetonitrile (250 mL)
5. 5
   ConcentraciónThe filtrate was concentrated in vacuo
6. 6
   Otrothe residue was purified by flash chromatography on silica gel (ethyl acetate)

Procedimiento

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)+.

Fuente