반응 #74159

반응 방정식

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

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

S-Phos

triethylamine

→

title compound

수율 80.0%

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

수율 80.0%

용매

toluene

반응 조건

후처리

1. 1
   기타irradiation in a sealed vial at 90° C. for 30 minutes
2. 2
   여과The mixture was then filtered through a celite pad
3. 3
   기타the filtrate evaporated in vacuo
4. 4
   세척washed with water
5. 5
   건조the organic layer dried over sodium sulphate
6. 6
   기타evaporated again
7. 7
   기타The crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 1%)

실험 절차

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.

출처