Reaktion #46598

Reaktionsgleichung

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

N-[1-(2-dimethylaminoethyl)-1H-indol-3-ylmethyl]-N-methyl-acrylamide

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Ausbeute 17.2%

(E)-N-[1-(2-dimethylaminoethyl)-1H-indol-3-ylmethyl]-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

Ausbeute 17.2%

Lösungsmittel

propionitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux under a N2 overnight
3. 3
   FiltrationThe dark mixture was filtered through a pad of Celite®
4. 4
   Waschenthe filter pad was rinsed with acetonitrile (250 mL)
5. 5
   EinengenThe filtrate was concentrated in vacuo
6. 6
   Sonstigethe residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3 containing 5% NH4OH in the MeOH)

Vorschrift

A solution of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (0.61 g, 2.70 mmole), N-[1-(2-dimethylaminoethyl)-1H-indol-3-ylmethyl]-N-methyl-acrylamide (1.00 g, 3.50 mmole), Pd(OAc)2 (0.08 g, 0.35 mmole), tri-ortho-tolylphosphine (0.21 g, 0.70 mmole), and diisopropylethylamine (0.91 mL, 5.25 mmole) in propionitrile (70 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 (250 mL). The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3 containing 5% NH4OH in the MeOH). The title compound (0.20 g. 13%) was obtained as a light yellow solid after drying in vacuo: MS (ES) m/e 432 (M+H)+.

Quelle