Reaktion #73796

Reaktionsgleichung

[2-(4-Bromo-phenyl)-2-(4-chloro-phenyl)ethyl]-methyl-amine

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

K3PO4

→

title compound

Ausbeute 84.2%

{2-(4-Chloro-phenyl)-2-[4-(1H-pyrazol-4-yl)-phenyl]-ethyl}-methyl-amine

Ausbeute 84.2%

Lösungsmittel

ethanol

methanol

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture purged with nitrogen for a further 2 minutes
2. 2
   SonstigeThe solvents were removed
3. 3
   Sonstigethe residue was partitioned between ethyl acetate and 2N NaOH
4. 4
   ExtraktionThe aqueous layer was extracted with ethyl acetate
5. 5
   Waschenthe combined organic layers were washed with brine
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe crude reaction mixture
9. 9
   Sonstigewas purified by column chromatography (SiO2)
10. 10
    Wascheneluting with dichloromethane:methanol:acetic acid:water (90:18:3:2)

Vorschrift

A solution of [2-(4-Bromo-phenyl)-2-(4-chloro-phenyl)ethyl]-methyl-amine (6.1 g, 13.716 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5.3 g, 27.431 mmol) and K3PO4 (10.19 g, 48.00 mmol) in ethanol (7.5 ml), methanol (11.5 ml), toluene (7.5 ml) and water (11.5 ml) was purged with nitrogen for 2 minutes. Bis(tri-t-butylphosphine)palladium (0) (175 mg, 2.5 mol %) was then added and the reaction mixture purged with nitrogen for a further 2 minutes. The mixture was then heated to 80° C., under nitrogen for a period of 17 hours. The solvents were removed and the residue was partitioned between ethyl acetate and 2N NaOH. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The crude reaction mixture was purified by column chromatography (SiO2), eluting with dichloromethane:methanol:acetic acid:water (90:18:3:2) to afford the title compound (3.6 g); LCMS (PS-A2) Rt 2.08 min [M+H]+ 312.

Quelle