Reacción #68655

Ecuación de reacción

4-bromopyrazole

1-iodobenzene

(+/−)-trans-1,2-diaminocyclohexane

potassium carbonate

N2

→

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

Disolventes

EtOAc

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONadded
2. 2
   Otrothe vessel sealed
3. 3
   Temperaturaheated to 100 C for 16 h
4. 4
   Lavadowashed with water
5. 5
   Otroan emullsion formed
6. 6
   OtroThe organic layer separated
7. 7
   Filtraciónthe aqueous emulsion mixture was filter through a pad of celite
8. 8
   Lavadorinsed with EtOAc, and sat. NaHCO3
9. 9
   SecadoThe combined organig layers were dried over Na2SO4
10. 10
    Filtraciónfiltered
11. 11
    Otroevaporate
12. 12
    OtroThe mixture was purified via flash chromatography
13. 13
    OtroThe title compound was collected as a yellow solid (3.18 g)

Procedimiento

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 emullsion 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 organig 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)

Fuente