Reaction #1583825

Reaction equation

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

Solvents

diethyl ether

toluene

methanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat refluxed for 24 h
3. 3
   TemperatureAfter cooling
4. 4
   Washwashed with water
5. 5
   DryingAfter drying over sodium sulfate
6. 6
   Otherthe solvent was removed under reduced pressure
7. 7
   OtherThe residue was purified by flash chromatography
8. 8
   Otherto afford a solid matieral (1.3 g), which
9. 9
   workup.ADDITIONa mixture of starting material

Procedure

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.

Source