Reaction #46592

Reaction equation

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

ethyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Yield 59.0%

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

Yield 59.0%

Solvents

propionitrile

DMF

Conditions

Workup

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

Procedure

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