반응 #46519

반응 방정식

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

tert-butyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

수율 162.4%

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

수율 162.4%

용매

propionitrile

DMF

반응 조건

후처리

1. 1
   온도at reflux overnight
2. 2
   여과The dark mixture was filtered through Celite®
3. 3
   농축the filtrate was concentrated

실험 절차

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)+.

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