Реакция #46592

Уравнение реакции

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

ethyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Выход 59.0%

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

Выход 59.0%

Растворители

propionitrile

DMF

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux overnight
3. 3
   ФильтрацияThe dark mixture was filtered through Celite®
4. 4
   Концентрированиеthe filtrate was concentrated

Методика

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)+.

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