Réaction #46592

Équation de réaction

6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one

ethyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Rendement 59.0%

Ethyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate

Rendement 59.0%

Solvants

propionitrile

DMF

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat reflux overnight
3. 3
   FiltrationThe dark mixture was filtered through Celite®
4. 4
   Concentrationthe filtrate was concentrated

Mode opératoire

A solution of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (5.0 g, 21.9 mmole), from Preparation 4, ethyl acrylate (3.3 g, 32.9 mmole), Pd(OAc)2 (1.1 g, 0.74 mmole), tri-ortho-tolylphosphine (1.3 g, 4.4 mmole), and diisopropylethylamine (11.4 mL, 65.7 mmole) in propionitrile (200 mL) and DMF (25 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (3.0 g, 59%) as a light yellow solid: MS (ES) m/e 233 (M+H)+.

Source