反応 #46519

反応方程式

5-bromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one

tert-butyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

収率 162.4%

tert-Butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate

収率 162.4%

溶媒

propionitrile

DMF

反応条件

後処理

1. 1
   温度at reflux overnight
2. 2
   ろ過The dark mixture was filtered through Celite®
3. 3
   濃縮the filtrate was concentrated

実験手順

A solution of 5-bromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (2.0 g, 9.49 mmole), tert-butyl acrylate (1.8 g, 14.1 mmole), Pd(OAc)2 (0.32 g, 1.4 mmole), tri-ortho-tolylphosphine (0.57 g, 1.9 mmole), and diisopropylethylamine (4.9 mL, 28.2 mmole) in propionitrile (100 mL) and DMF (10 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (0.80 g, 33%) as a light yellow solid. MS (ES) m/e 261 (M+H)+.

出典