反応 #306434

反応方程式

4-bromopyrazole

1-iodobenzene

(+/−)-trans-1,2-diaminocyclohexane

potassium carbonate

N2

→

4-bromo-1-phenyl-1H-pyrazole

溶媒

EtOAc

dioxane

反応条件

後処理

1. 1
   workup.ADDITIONadded
2. 2
   その他the vessel sealed
3. 3
   温度heated to 100 C for 16 h
4. 4
   洗浄washed with water
5. 5
   その他an emulsion formed
6. 6
   その他The organic layer separated
7. 7
   ろ過the aqueous emulsion mixture was filter through a pad of celite
8. 8
   洗浄rinsed with EtOAc, and sat. NaHCO3
9. 9
   乾燥The combined organic layers were dried over Na2SO4
10. 10
    ろ過filtered
11. 11
    その他evaporate
12. 12
    その他The mixture was purified via flash chromatography
13. 13
    その他The title compound was collected as a yellow solid (3.18 g)

実験手順

A sealable tube was charged with 4-bromopyrazole (4.000 g, 27.2 mmol), 1-iodobenzene (3.64 ml, 32.7 mmol), (+/−)-trans-1,2-diaminocyclohexane (0.654 ml, 5.44 mmol), Copper iodide (I) (0.518 g, 2.72 mmol), potassium carbonate (8.28 g, 59.9 mmol) and 13 mL dioxane added. The mixture was blanketed with N2, the vessel sealed and heated to 100 C for 16 h. The mixture was allowed to cool to rt, diluted with EtOAc, washed with water, and an emulsion formed. The organic layer separated and the aqueous emulsion mixture was filter through a pad of celite and rinsed with EtOAc, and sat. NaHCO3. The combined organic layers were dried over Na2SO4, filtered and evaporate. The mixture was purified via flash chromatography using a 0% to 100% CH2Cl2 in hexanes gradient. The title compound was collected as a yellow solid (3.18 g)

出典