Reacción #46596

Ecuación de reacción

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

N-(1H-indol-3-ylmethyl)-N-methylacrylamide

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Rendimiento 37.0%

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

Rendimiento 37.0%

Disolventes

propionitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux under N2 overnight
3. 3
   FiltraciónThe dark mixture was filtered through a pad of Celite®
4. 4
   Lavadothe filter pad was rinsed with acetonitrile (250 mL)
5. 5
   ConcentraciónThe filtrate was concentrated in vacuo
6. 6
   Otrothe residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3)

Procedimiento

A solution of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (0.64 g, 2.80 mmole), N-(1H-indol-3-ylmethyl)-N-methylacrylamide (0.60 g, 2.80 mmole), Pd(OAc)2 (0.06 g, 0.28 mmole), tri-ortho-tolylphosphine (0.17 g, 0.56 mmole) and diisopropylethylamine (0.73 mL, 4.2 mmole) in propionitrile (50 mL) was deoxygenated, then was heated to reflux under N2 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 (10% MeOH/CHCl3). The title compound (0.37 g, 37%) was obtained as a light yellow solid after drying in vacuo: MS (ES) m/e 361 (M+H)+.

Fuente