Reaktion #68655

Reaktionsgleichung

4-bromopyrazole

1-iodobenzene

(+/−)-trans-1,2-diaminocyclohexane

potassium carbonate

N2

→

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

Lösungsmittel

EtOAc

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONadded
2. 2
   Sonstigethe vessel sealed
3. 3
   Temperaturheated to 100 C for 16 h
4. 4
   Waschenwashed with water
5. 5
   Sonstigean emullsion formed
6. 6
   SonstigeThe organic layer separated
7. 7
   Filtrationthe aqueous emulsion mixture was filter through a pad of celite
8. 8
   Waschenrinsed with EtOAc, and sat. NaHCO3
9. 9
   TrocknenThe combined organig layers were dried over Na2SO4
10. 10
    Filtrationfiltered
11. 11
    Sonstigeevaporate
12. 12
    SonstigeThe mixture was purified via flash chromatography
13. 13
    SonstigeThe title compound was collected as a yellow solid (3.18 g)

Vorschrift

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)

Quelle