Reaktion #591534

Reaktionsgleichung

1-(4-bromophenyl)cyclopropanecarbonitrile

3-(trifluoromethyl)-1H-pyrazole

toluene

N,N-dimethylformamide

(1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine

potassium carbonate

→

1-{4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}cyclopropanecarbonitrile

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was microwave irradiated at 200° C. for 60 minutes
2. 2
   Filtrationfiltered
3. 3
   workup.ADDITIONThe filtrate was diluted with methanol
4. 4
   Sonstigethe product from the filtrate was isolated
5. 5
   Sonstigepurified
6. 6
   SonstigeAdditional product could be obtained from the precipitate
7. 7
   Waschenwashing with satd
8. 8
   TrocknenNaHCO3, brine, drying with MgSO4
9. 9
   Einengenconcentrating for purification

Vorschrift

To a solution of 1-(4-bromophenyl)cyclopropanecarbonitrile (600 mg, 0.003 mol), 3-(trifluoromethyl)-1H-pyrazole (441 mg, 0.00324 mol) in toluene (2 mL, 0.02 mol) and N,N-dimethylformamide (3 mL, 0.04 mol) were added (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (77 mg, 0.00054 mol), copper(I) iodide (51 mg, 0.00027 mol), and potassium carbonate (784 mg, 0.00567 mol). The mixture was microwave irradiated at 200° C. for 60 minutes and then filtered. The filtrate was diluted with methanol, and the product from the filtrate was isolated and purified using prep-HPLC. Additional product could be obtained from the precipitate by dissolving the precipitate in EtOAc, washing with satd. NaHCO3, brine, drying with MgSO4, and concentrating for purification.

Quelle