Reacción #1583825

Ecuación de reacción

methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate

product

methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate

[3-(trifluoromethoxy)phenyl]boronic acid

cesium carbonate

triphenylphosphine

→

title compound

methyl 2-[4-chloro-3′-(trifluoromethoxy)[1,1′-biphenyl]-3-yl]hydrazine carboxylate

Disolventes

diethyl ether

toluene

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat refluxed for 24 h
3. 3
   TemperaturaAfter cooling
4. 4
   Lavadowashed with water
5. 5
   SecadoAfter drying over sodium sulfate
6. 6
   Otrothe solvent was removed under reduced pressure
7. 7
   OtroThe residue was purified by flash chromatography
8. 8
   Otroto afford a solid matieral (1.3 g), which
9. 9
   workup.ADDITIONa mixture of starting material

Procedimiento

A mixture of methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate (i.e. the product of Step B) (1.27 g, 4.5 mmol), [3-(trifluoromethoxy)phenyl]boronic acid (1.85 g, 9 mmol), cesium carbonate (2.9 g, 9 mmol), tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) and triphenylphosphine (1.2 g, 4.5 mmol) in toluene (60 mL) and methanol (60 mL) was heated at refluxed for 24 h. After cooling, the reaction mixture was taken up in diethyl ether and washed with water. After drying over sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by flash chromatography using 25% ethyl acetate in hexanes as eluant to afford a solid matieral (1.3 g), which was a mixture of starting material and the title compound.

Fuente