反応 #74159

反応方程式

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

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

S-Phos

triethylamine

→

title compound

収率 80.0%

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

収率 80.0%

溶媒

toluene

反応条件

後処理

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

実験手順

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.

出典