تفاعل #46592

معادلة التفاعل

6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one

ethyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

المردود 59.0%

Ethyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate

المردود 59.0%

المذيبات

propionitrile

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةat reflux overnight
3. 3
   ترشيحThe dark mixture was filtered through Celite®
4. 4
   تركيزthe filtrate was concentrated

الإجراء التجريبي

A solution of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (5.0 g, 21.9 mmole), from Preparation 4, ethyl acrylate (3.3 g, 32.9 mmole), Pd(OAc)2 (1.1 g, 0.74 mmole), tri-ortho-tolylphosphine (1.3 g, 4.4 mmole), and diisopropylethylamine (11.4 mL, 65.7 mmole) in propionitrile (200 mL) and DMF (25 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (3.0 g, 59%) as a light yellow solid: MS (ES) m/e 233 (M+H)+.

المصدر