Reacción #46601

Ecuación de reacción

(E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]acrylic acid hydrochloride salt

2-methyl-3-(methylaminomethyl)indole

Et3N

HOBt H2O

EDC

→

title compound

Rendimiento 73.0%

(E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)acrylamide

Rendimiento 73.0%

Disolventes

DMF CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónwas concentrated to dryness
2. 2
   Lavadothe solution was washed with H2O
3. 3
   Secadobrine, dried (Na2SO4)
4. 4
   Concentraciónconcentrated under vacuum
5. 5
   OtroThe remaining residue was purified by flash chromatography on silica gel (4% MeOH/CHCl3)

Procedimiento

To a stirred solution of (E)-3-[6-[N-(methoxycarbonylmethyl)amino]pyridin-3-yl]acrylic acid hydrochloride salt (2.0 g, 7.3 mmole) in 1:1 DMF/CH2Cl2 (100 mL) was added 2-methyl-3-(methylaminomethyl)indole (1.3 g, 7.5 mmole), Et3N (2.1 mL, 15 mmole), and HOBt H2O (1.0 g, 7.4 mmole), followed by EDC (1.4 g, 7.3 mmole). After stirring at room temperature for 18 h the reaction was concentrated to dryness. The residue was taken up in EtOAc, and the solution was washed with H2O then brine, dried (Na2SO4), and concentrated under vacuum. The remaining residue was purified by flash chromatography on silica gel (4% MeOH/CHCl3) to give the title compound (2.08 g, 73%) as an off-white solid: MS (ES) m/e 393.2 (M+H)+.

Fuente