反应 #73880

反应方程式

1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

2,6-dibromopyridine

cesium carbonate

BINAP

→

title compound

1-(4′-{3-Methyl-4-[6-bromo-pyridin-2-ylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

溶剂

EtOAc

THF

反应条件

后处理

1. 1
   其他bubbled with nitrogen for 1 hr
2. 2
   温度cooled to room temperature
3. 3
   萃取extracted with H2O (2×100 mL)
4. 4
   干燥The organic layer was dried over MgSO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated
7. 7
   其他the crude residue was purified on silica gel (0% to 80% EtOAc in hexane gradient)

实验过程

1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (2.7 g, 6.7 mmol), 2,6-dibromopyridine (2.3 g, 10.0 mmol), cesium carbonate (3.04 g, 9.4 mmol), and BINAP (0.187 g, 0.3 mmol) were stirred in THF (100 mL) at room temperature and bubbled with nitrogen for 1 hr. Palladium(II) acetate (0.068 g, 0.20 mmol) was added, and the mixture was warmed to 70° C., stirred for 72 hrs, then cooled to room temperature. The resulting mixture was diluted with EtOAc (300 mL) and extracted with H2O (2×100 mL). The organic layer was dried over MgSO4, filtered and concentrated, and the crude residue was purified on silica gel (0% to 80% EtOAc in hexane gradient) to afford the title compound.

来源