تفاعل #74159

معادلة التفاعل

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

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

S-Phos

triethylamine

→

title compound

المردود 80.0%

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

المردود 80.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىirradiation in a sealed vial at 90° C. for 30 minutes
2. 2
   ترشيحThe mixture was then filtered through a celite pad
3. 3
   أخرىthe filtrate evaporated in vacuo
4. 4
   غسيلwashed with water
5. 5
   تجفيفthe organic layer dried over sodium sulphate
6. 6
   أخرىevaporated again
7. 7
   أخرىThe crude was finally purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 1%)

الإجراء التجريبي

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.

المصدر