Reacción #46610

Ecuación de reacción

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

Rendimiento 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

Rendimiento 25.0%

Disolventes

propionitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was heated
2. 2
   Temperaturaat reflux under argon for 10 h
3. 3
   Filtraciónfiltered through supercel
4. 4
   ConcentraciónThe filtrate was concentrated
5. 5
   Otrothe residue was purified by flash chromatography on silica gel

Procedimiento

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.

Fuente