Reacción #46519

Ecuación de reacción

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

tert-butyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Rendimiento 162.4%

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

Rendimiento 162.4%

Disolventes

propionitrile

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux overnight
2. 2
   FiltraciónThe dark mixture was filtered through Celite®
3. 3
   Concentraciónthe filtrate was concentrated

Procedimiento

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)+.

Fuente