Reaction #46594

Reaction equation

EDC

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

1-isopropyl-3-(methylaminomethyl)indole

HOBt H2O

diisopropylethylamine

→

title compound

Yield 58.6%

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

Yield 58.6%

Solvents

DMF

Conditions

Workup

1. 1
   Concentrationthen was concentrated in vacuo
2. 2
   workup.ADDITIONThe residue was diluted with water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe combined organic extracts were washed with brine
5. 5
   Dryingdried over Na2SO4

Procedure

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)+.

Source