反応 #46626

反応方程式

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

収率 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

収率 36.0%

溶媒

propionitrile

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux under N2 overnight
3. 3
   ろ過The dark mixture was filtered through a pad of Celite®
4. 4
   洗浄the filter pad was rinsed with acetonitrile (250 mL)
5. 5
   濃縮The filtrate was concentrated in vacuo
6. 6
   その他the residue was purified by flash chromatography on silica gel (10% EtOAc/EtOH)

実験手順

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)+.

出典