Reaktion #46610

Reaktionsgleichung

N-methyl-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamide

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

DIEA

tri-o-tolylphosphine

→

title compound

Ausbeute 25.0%

(E)-N-Methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)-acrylamide

Ausbeute 25.0%

Lösungsmittel

propionitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturat reflux under argon for 10 h
3. 3
   Filtrationfiltered through supercel
4. 4
   EinengenThe filtrate was concentrated
5. 5
   Sonstigethe residue was purified by flash chromatography on silica gel

Vorschrift

A mixture of N-methyl-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamide (256 mg, 1 mmole) and 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (227 mg, 1 mmole) in propionitrile (20 mL) was treated with DIEA (0.3 mL), Pd(OAc)2 (29 mg, 0.13 mmole), and tri-o-tolylphosphine (50 mg, 0.16 mmole). The reaction was heated at reflux under argon for 10 h, then was cooled to RT and filtered through supercel. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel to afford the title compound (100 mg, 25%) as an off-white solid: MS (ES) m/e 403.2 (M+H)+. Anal. Calcd for C24H26N4O2.2.75H2O: C, 63.77; H, 7.02; N, 12.39. Found: C, 63.81; H, 7.25; N, 11.90.

Quelle