Reacción #46589

Ecuación de reacción

(E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylic acid hydrochloride salt

hydroxybenzotriazole monohydrate

diisopropylethylamine

2-methyl-3-(methylaminomethyl)indole

EDC

→

title compound

Rendimiento 88.0%

(E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylamide

Rendimiento 88.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónAfter 12 hr the reaction solution was concentrated under vacuum
2. 2
   Otrothe residue was purified by flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH)

Procedimiento

To a solution of (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylic acid hydrochloride salt (0.50 g, 2.1 mmole), hydroxybenzotriazole monohydrate (0.31 g, 2.3 mmole), diisopropylethylamine (0.80 mL, 4.6 mmole), and 2-methyl-3-(methylaminomethyl)indole (0.40 g, 2.3 mmole) in DMF (50 mL) at RT was added EDC (0.46, 2.3 mmole). After 12 hr the reaction solution was concentrated under vacuum and the residue was purified by flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) to give the title compound (0.66 g, 88%) as a light yellow solid: MS (ES) m/e 361 (M+H)+.

Fuente