Reaktion #46592

Reaktionsgleichung

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

ethyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Ausbeute 59.0%

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

Ausbeute 59.0%

Lösungsmittel

propionitrile

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux overnight
3. 3
   FiltrationThe dark mixture was filtered through Celite®
4. 4
   Einengenthe filtrate was concentrated

Vorschrift

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)+.

Quelle