Reacción #48069

Ecuación de reacción

3-bromo-4-fluorophenylamine

cyclopropyl boronic acid

potassium phosphate

tricyclohexyl phosphine

→

3-cyclopropyl-4-fluorophenylamine

Rendimiento 64.0%

Disolventes

toluene

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was then cooled to RT
2. 2
   Extracciónextracted with ether
3. 3
   Lavadowashed with brine
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   Otroto give a residue which
8. 8
   Otrowas purified by flash column chromatography

Procedimiento

To a solution of 3-bromo-4-fluorophenylamine (synthesized as described in J. Org. Chem. 1981, 46, 2280-2286) (415 mg, 2.18 mmol), cyclopropyl boronic acid (244 mg, 2.84 mmol), potassium phosphate (1.62 g, 7.64 mmol), and tricyclohexyl phosphine (61 mg, 0.22 mmol) in toluene (10 ml) and water (0.5 ml) was added palladium acetate (25 mg, 0.11 mmol) and the reaction mixture was heated to 100° C. overnight. The mixture was then cooled to RT and diluted with water and extracted with ether. The organic phases were combined, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography to give 3-cyclopropyl-4-fluorophenylamine (210 mg, 64%). MS (ISP) 152.2 (M+H)+.

Fuente