반응 #46601

반응 방정식

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

2-methyl-3-(methylaminomethyl)indole

Et3N

HOBt H2O

EDC

→

title compound

수율 73.0%

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

수율 73.0%

용매

DMF CH2Cl2

반응 조건

후처리

1. 1
   농축was concentrated to dryness
2. 2
   세척the solution was washed with H2O
3. 3
   건조brine, dried (Na2SO4)
4. 4
   농축concentrated under vacuum
5. 5
   기타The remaining residue was purified by flash chromatography on silica gel (4% MeOH/CHCl3)

실험 절차

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)+.

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