반응 #46599

반응 방정식

3-bromo-5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one

N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

수율 57.1%

(E)-N-methyl-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamide

수율 57.1%

용매

propionitrile

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux under a N2 overnight
3. 3
   여과The dark mixture was filtered through a pad of Celite®
4. 4
   세척the filter pad was rinsed with acetonitrile (200 mL)
5. 5
   농축The filtrate was concentrated in vacuo
6. 6
   기타the residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3)

실험 절차

A solution of 3-bromo-5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one (0.60 g, 2.50 mmole), N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide (0.85 g, 3.75 mmole), Pd(OAc)2 (0.06 g, 0.25 mmole), tri-ortho-tolylphosphine (0.15 g, 0.50 mmole) and diisopropylethylamine (0.87 mL, 5.00 mmole) in propionitrile (50 mL) was deoxygenated, then was and heated to reflux under a N2 overnight. The dark mixture was filtered through a pad of Celite®, and the filter pad was rinsed with acetonitrile (200 mL). The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3). The title compound (0.35 g. 35%) was obtained as a light tan solid after drying in vacuo: MS (ES) m/e 246 (M+H)+.

출처