反应 #74159

反应方程式

4-iodo-1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazole

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

S-Phos

triethylamine

→

title compound

收率 80.0%

1-(4-methoxybenzyl)-3-(3-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

收率 80.0%

溶剂

toluene

反应条件

后处理

1. 1
   其他irradiation in a sealed vial at 90° C. for 30 minutes
2. 2
   过滤The mixture was then filtered through a celite pad
3. 3
   其他the filtrate evaporated in vacuo
4. 4
   洗涤washed with water
5. 5
   干燥the organic layer dried over sodium sulphate
6. 6
   其他evaporated again
7. 7
   其他The crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 1%)

实验过程

1 g (2.3 mmol) of 4-iodo-1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazole (prepared as described in Example 27) was dissolved in 20 ml of dry toluene and 3.18 ml of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (23 mmol), 20 mg (0.08 mmol) of palladium(II) chloride diacetonitrile complex, 80 mg (0.005 mmol) of S-Phos (2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl) and 774 μl (5.7 mmol) of triethylamine were added successively. The reaction mixture was submitted to microwave irradiation in a sealed vial at 90° C. for 30 minutes. The mixture was then filtered through a celite pad and the filtrate evaporated in vacuo. The residue was taken up with dichloromethane and washed with water and the organic layer dried over sodium sulphate and evaporated again. The crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 1%), affording 800 mg (80%) of the title compound, crystallized from diethylether.

来源