Реакция #46626

Уравнение реакции

6-bromo-3-(2-methoxyethyl)-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one

diisopropylethylamine

tri-ortho-tolylphosphine

N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide

→

title compound

Выход 36.0%

(E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-[3-(2-methoxyethyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-6-yl]acrylamide

Выход 36.0%

Растворители

propionitrile

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat 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% EtOAc/EtOH)

Методика

A solution of 6-bromo-3-(2-methoxyethyl)-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one (0.86 g, 3.00 mmole), N-(2-methyl-1H-indol-3-ylmethyl)-N-methylacrylamide (see Example 1 (a), 0.68 g, 3.00 mmole), Pd(OAc)2 (0.07 g, 0.30 mmole), tri-ortho-tolylphosphine (0.18 g, 0.60 mmole) and diisopropylethylamine (1.31 mL, 7.50 mmole) in propionitrile (50 mL) was deoxygenated, then was heated at 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% EtOAc/EtOH). The title compound (0.46 g, 36%) was obtained as a light yellow solid after drying in vacuo: MS (ES) m/e 434 (M+H)+.

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