Reaktion #46519

Reaktionsgleichung

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

tert-butyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Ausbeute 162.4%

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

Ausbeute 162.4%

Lösungsmittel

propionitrile

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux overnight
2. 2
   FiltrationThe dark mixture was filtered through Celite®
3. 3
   Einengenthe filtrate was concentrated

Vorschrift

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)+.

Quelle