反応 #74133

反応方程式

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

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

cesium carbonate

→

4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine

溶媒

dioxane

water

反応条件

後処理

1. 1
   その他irradiation at 120° C. for 30 minutes in a sealed vial
2. 2
   ろ過The reaction was filtered through a celite pad
3. 3
   その他the solvent evaporated to dryness
4. 4
   その他The crude was then partitioned between dichloromethane and water
5. 5
   乾燥the organic layer dried over sodium sulphate
6. 6
   その他the solvent removed in vacuo
7. 7
   その他After purification by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3) 78 mg (88%) of the title compound
8. 8
   その他were obtained

実験手順

To a solution of 100 mg (0.23 mol) of 4-iodo-1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazole in 16 ml of dioxane and 4 ml of water, 90 mg (0.46 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 52 mg (0.046 mmol) of palladium tetrakis and 150 mg (0.46 mmol) mg of cesium carbonate were added successively. The mixture was submitted to microwave irradiation at 120° C. for 30 minutes in a sealed vial. The reaction was filtered through a celite pad and the solvent evaporated to dryness. The crude was then partitioned between dichloromethane and water, the organic layer dried over sodium sulphate and the solvent removed in vacuo. After purification by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3) 78 mg (88%) of the title compound were obtained.

出典