반응 #46626

반응 방정식

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

수율 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

수율 36.0%

용매

propionitrile

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux under N2 overnight
3. 3
   여과The dark mixture was filtered through a pad of Celite®
4. 4
   세척the filter pad was rinsed with acetonitrile (250 mL)
5. 5
   농축The filtrate was concentrated in vacuo
6. 6
   기타the residue was purified by flash chromatography on silica gel (10% EtOAc/EtOH)

실험 절차

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)+.

출처