Reaktion #167287

Reaktionsgleichung

1-naphthalen-2-yl-imidazolidin-2-one

trans-1,2-diamino cyclohexane

potassium carbonate

3-bromo-5-trifluoromethyl-pyridine

→

1-naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one

Ausbeute 52.0%

Lösungsmittel

ethyl acetate

1,4-dioxane

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepreviously degassed with argon (10 minutes)
2. 2
   SonstigeThe reaction was purged with argon for a further 10 minutes
3. 3
   Temperaturthe resulting mixture was heated
4. 4
   FiltrationThe reaction mixture was filtered through celite
5. 5
   Waschenthe bed was washed with chloroform
6. 6
   SonstigeThe organic layer was dried over Na2O4
7. 7
   Einengenconcentrated
8. 8
   SonstigePurification by column chromatography (using silica gel of mesh size of 60-120, 30% EtOAc in hexane as eluant)

Vorschrift

Copper iodide (12.6 mg, 0.066 mmol), trans-1,2-diamino cyclohexane (22.79 mg, 0.199 mmol) and potassium carbonate (183.5 mg, 1.32 mmol) were added to 1,4-dioxane (5 mL) and 3-bromo-5-trifluoromethyl-pyridine (150 mg, 0.66 mmol) previously degassed with argon (10 minutes). The reaction was purged with argon for a further 10 minutes, followed by the addition of 1-naphthalen-2-yl-imidazolidin-2-one (I-79b: 140 mg, 0.66 mmol) and the resulting mixture was heated to reflux at 110° C. for 15 hours. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was filtered through celite and the bed was washed with chloroform. The organic layer was dried over Na2O4 and concentrated. Purification by column chromatography (using silica gel of mesh size of 60-120, 30% EtOAc in hexane as eluant) afforded 120 mg (52% yield) of 1-naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one.

Quelle