Reacción #46597

Ecuación de reacción

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

N-(1-benzyl-1H-indol-3-ylmethyl)-N-methyl-acrylamide

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Rendimiento 35.0%

(E)-N-(1-benzyl-1H-indol-3-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

Rendimiento 35.0%

Disolventes

propionitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux under a N2 overnight
3. 3
   FiltraciónThe dark mixture was filtered through a pad of Celite®
4. 4
   Lavadothe filter pad was rinsed with acetonitrile (300 mL)
5. 5
   ConcentraciónThe filtrate was concentrated in vacuo
6. 6
   Otrothe residue was purified by flash chromatography on silica gel (5% MeOH/CHCl3)

Procedimiento

A solution of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (1.05 g, 4.60 mmole), N-(1-benzyl-1H-indol-3-ylmethyl)-N-methyl-acrylamide (1.40 g, 4.60 mmole), Pd(OAc)2 (0.10 g, 0.46 mmole), tri-ortho-tolylphosphine (0.28 g, 0.92 mmole) and diisopropylethylamine (1.20 mL 6.90 mmole) in propionitrile (75 mL) was deoxygenated, then was and heated to reflux under a N2 overnight. The dark mixture was filtered through a pad of Celite®, and the filter pad was rinsed with acetonitrile (300 mL). The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (5% MeOH/CHCl3). The title compound (0.70 g. 35%) was obtained as a light yellow solid after drying in vacuo: MS (ES) m/e 451 (M+H)+.

Fuente