Reaktion #46593

Reaktionsgleichung

EDC

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

1-ethyl-3-(methylaminomethyl)-1H-indole

HOBt H2O

diisopropylethylamine

→

title compound

Ausbeute 52.0%

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

Ausbeute 52.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthen was concentrated in vacuo
2. 2
   workup.ADDITIONThe residue was diluted with water
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe combined organic extracts were washed with brine
5. 5
   Trocknendried over Na2SO4

Vorschrift

EDC (0.56 g, 2.93 mmole) was added to a solution of (E)-3-(6-aminopyridin-3-yl)acrylic acid (0.48 g, 2.93 mmole), 1-ethyl-3-(methylaminomethyl)-1H-indole (0.50 g. 2.66 mmole), HOBt H2O (0.40 g, 2.93 mmole) and diisopropylethylamine (0.93 mL, 5.32 mmole) in DMF (30 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 title compound (0.46 g, 52%) as a yellow solid after drying in vacuo: MS (ES) m/e 335 (M+H)+.

Quelle