Reacción #46594

Ecuación de reacción

EDC

(E)-3-(6-aminopyridin-3-yl)acrylic acid

1-isopropyl-3-(methylaminomethyl)indole

HOBt H2O

diisopropylethylamine

→

title compound

Rendimiento 58.6%

(E)-3-(6-aminopyridin-3-yl)-N-(1-isopropyl-1H-indol-3-ylmethyl)-N-methylacrylamide

Rendimiento 58.6%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthen was concentrated in vacuo
2. 2
   workup.ADDITIONThe residue was diluted with water
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe combined organic extracts were washed with brine
5. 5
   Secadodried over Na2SO4

Procedimiento

EDC (0.51 g, 2.64 mmole) was added to a solution of (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.43 g, 2.64 mmole), 1-isopropyl-3-(methylaminomethyl)indole (0.49 g, 2.40 mmole), HOBt H2O (0.36 g, 2.64 mmole) and diisopropylethylamine (0.84 mL 4.80 mmole) in DMF (40 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Flash chromatography on silica gel (10% MeOH/CHCl3) gave the title compound (0.49 g, 58%) as a yellow solid after drying in vacuo: MS (ES) m/e 349 (M+H)+.

Fuente