Nitrogen → 4-Bromo-1-phenyl-1H-pyrazole

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)

1. additionadded
2. customthe vessel sealed
3. temperatureheated to 100 C for 16 h
4. washwashed with water
5. customan emullsion formed
6. customThe organic layer separated
7. filtrationthe aqueous emulsion mixture was filter through a pad of celite
8. washrinsed with EtOAc, and sat. NaHCO3
9. dry with materialThe combined organig layers were dried over Na2SO4
10. filtrationfiltered
11. customevaporate
12. customThe mixture was purified via flash chromatography
13. customThe title compound was collected as a yellow solid (3.18 g)

ORD-Eintrag

ord-5aeb37f62849404ab729720b2c74811c

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08524900B2