تفاعل #46519

معادلة التفاعل

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

tert-butyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

المردود 162.4%

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

المردود 162.4%

المذيبات

propionitrile

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux overnight
2. 2
   ترشيحThe dark mixture was filtered through Celite®
3. 3
   تركيزthe filtrate was concentrated

الإجراء التجريبي

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)+.

المصدر