Reaktion #46601

Reaktionsgleichung

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

2-methyl-3-(methylaminomethyl)indole

Et3N

HOBt H2O

EDC

→

title compound

Ausbeute 73.0%

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

Ausbeute 73.0%

Lösungsmittel

DMF CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenwas concentrated to dryness
2. 2
   Waschenthe solution was washed with H2O
3. 3
   Trocknenbrine, dried (Na2SO4)
4. 4
   Einengenconcentrated under vacuum
5. 5
   SonstigeThe remaining residue was purified by flash chromatography on silica gel (4% MeOH/CHCl3)

Vorschrift

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)+.

Quelle