تفاعل #46601

معادلة التفاعل

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

2-methyl-3-(methylaminomethyl)indole

Et3N

HOBt H2O

EDC

→

title compound

المردود 73.0%

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

المردود 73.0%

المذيبات

DMF CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   تركيزwas concentrated to dryness
2. 2
   غسيلthe solution was washed with H2O
3. 3
   تجفيفbrine, dried (Na2SO4)
4. 4
   تركيزconcentrated under vacuum
5. 5
   أخرىThe remaining residue was purified by flash chromatography on silica gel (4% MeOH/CHCl3)

الإجراء التجريبي

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)+.

المصدر