Reacción #167205

Ecuación de reacción

trans-1,2-diamino cyclohexane

potassium carbonate

1-pyridin-3-yl-imidazolidin-2-one

2-bromo naphthalene

→

1-naphthalen-2-yl-3-pyridin-3-yl-imidazolidin-2-one

Rendimiento 28.0%

Disolventes

MeOH

1,4-dioxane

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropreviously purged with argon (10 minutes)
2. 2
   OtroThe reaction mixture was purged with argon for 10 minutes
3. 3
   TemperaturaThe reaction mixture was heated
4. 4
   FiltraciónThe reaction mixture was filtered through a celite bed
5. 5
   Lavadothe bed was washed with chloroform
6. 6
   ConcentraciónThe organic layer was concentrated
7. 7
   Otropurification by column chromatography (using silica gel of mesh size of 60-120, 20% ethyl acetate in hexane as eluent)

Procedimiento

Copper iodide (10.0 mg, 0.113 mmol), trans-1,2-diamino cyclohexane (10.0 mg, 0.091 mmol) and potassium carbonate (169 mg, 1.22 mmol) were added to a solution of 1,4-dioxane (5 mL) previously purged with argon (10 minutes). The reaction mixture was purged with argon for 10 minutes, followed by the addition of 1-pyridin-3-yl-imidazolidin-2-one (I-1b: 100 mg, 0.61 mmol) and 2-bromo naphthalene (126 mg, 0.61 mmol). The reaction mixture was heated to reflux at 110° C. for 15 hours. The reaction was monitored by TLC (10% MeOH in chloroform). The reaction mixture was filtered through a celite bed and the bed was washed with chloroform. The organic layer was concentrated and purification by column chromatography (using silica gel of mesh size of 60-120, 20% ethyl acetate in hexane as eluent) afforded 48 mg (28% yield) of 1-naphthalen-2-yl-3-pyridin-3-yl-imidazolidin-2-one.

Fuente