Reaktion #46596

Reaktionsgleichung

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

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

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Ausbeute 37.0%

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

Ausbeute 37.0%

Lösungsmittel

propionitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux under 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)

Vorschrift

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)+.

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