反应 #617

ord-d3fce1c8e3204b57a80e5c0d53c5c1f7

反应方程式

COc1ccc(NC(C)=O)cc1Br
COc1ccc(NC(C)=O)cc1B
CC(C)(C)OC(=O)N1CCNCC1
CC(C)(C)OC(=O)N1CCNC
COc1ccc(NC(C)=O)cc1N1CCNCC1
COc1ccc(NC(C)=O)cc1N
收率 50.9%

溶剂

反应条件

温度
100°CELSIUS

实验过程

A solution of N-(3-bromo-4-methoxyphenyl)acetamide (0.5 g, 2.05 mmol) dissolved in toluene (5 mL) was treated with tert-butyl piperazine-1-carboxylate (0.382 g, 2.05 mmol), diacetoxypalladium (0.046 g, 0.20 mmol), dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine (0.191 g, 0.41 mmol) and sodium 2-methylpropan-2-olate (0.433 g, 4.51 mmol) in a sealed tube. The resulting mixture was degassed and stirred at 100 °C for 8 hours in a microwave. The mixture was pre-absorbed onto silica. The crude product was purified by flash silica chromatography, elution 50% ethyl acetate in Heptane. Pure fractions were evaporated to dryness to afford intermediate. The intermediate was dissolved in 4M HCl in dioxane (10mL) and stirred at RT overnight. The mixture was evaporated to give N-(4-methoxy-3-(piperazin-1-yl)phenyl)acetamide (0.260 g, 50.9 %) as a tan solid.

来源

750 AstraZeneca ELN dataset