Reacción #170746

Ecuación de reacción

sodium carbonate

tricyclohexylphosphine

sodium hydrogen carbonate

5-iodo-1-phenyl-1H-pyrazol-3-ylamine

2-(3-butylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

→

titled compound

Rendimiento 86.1%

5-(3-Butylphenyl)-1-phenyl-1H-pyrazol-3-ylamine

Rendimiento 86.1%

Disolventes

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 3 hours
2. 2
   Filtraciónthe insoluble substance was filtered off through Celite
3. 3
   ExtracciónThe filtrate was extracted with ethyl acetate
4. 4
   Lavadothe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1 to 2/3)

Procedimiento

To a solution of 5-iodo-1-phenyl-1H-pyrazol-3-ylamine (1.00 g) prepared according to the same procedures as Preparation 2 in 1,2-dimethoxyethane (20 ml) were sequentially added 2-(3-butylphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1.37 g), a 2M aqueous solution of sodium carbonate (10 ml), tricyclohexylphosphine (197 mg) and palladium acetate (79 mg) at room temperature, and the mixture was stirred at reflux for 3 hours. This reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added thereto, and then the insoluble substance was filtered off through Celite. The filtrate was extracted with ethyl acetate, the resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1 to 2/3) to give the titled compound (880 mg).

Fuente