Реакция #46596

Уравнение реакции

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

N-(1H-indol-3-ylmethyl)-N-methylacrylamide

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Выход 37.0%

(E)-N-(1H-indol-3-ylmethyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

Выход 37.0%

Растворители

propionitrile

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураto reflux under N2 overnight
3. 3
   ФильтрацияThe dark mixture was filtered through a pad of Celite®
4. 4
   Промывкаthe filter pad was rinsed with acetonitrile (250 mL)
5. 5
   КонцентрированиеThe filtrate was concentrated in vacuo
6. 6
   Другоеthe residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3)

Методика

A solution of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (0.64 g, 2.80 mmole), N-(1H-indol-3-ylmethyl)-N-methylacrylamide (0.60 g, 2.80 mmole), Pd(OAc)2 (0.06 g, 0.28 mmole), tri-ortho-tolylphosphine (0.17 g, 0.56 mmole) and diisopropylethylamine (0.73 mL, 4.2 mmole) in propionitrile (50 mL) was deoxygenated, then was heated to reflux under N2 overnight. The dark mixture was filtered through a pad of Celite®, and the filter pad was rinsed with acetonitrile (250 mL). The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3). The title compound (0.37 g, 37%) was obtained as a light yellow solid after drying in vacuo: MS (ES) m/e 361 (M+H)+.

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