Réaction #46572

Équation de réaction

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

Rendement 58.5%

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

Rendement 58.5%

Solvants

propionitrile

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureat reflux overnight
3. 3
   FiltrationThe dark mixture was filtered through a pad of Celite®
4. 4
   Lavagethe filter pad was rinsed with acetonitrile (250 mL)
5. 5
   ConcentrationThe filtrate was concentrated in vacuo
6. 6
   Autrethe residue was purified by flash chromatography on silica gel (ethyl acetate)

Mode opératoire

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)+.

Source