Réaction #1583825

Équation de réaction

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

Solvants

diethyl ether

toluene

methanol

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat refluxed for 24 h
3. 3
   TempératureAfter cooling
4. 4
   Lavagewashed with water
5. 5
   SéchageAfter drying over sodium sulfate
6. 6
   Autrethe solvent was removed under reduced pressure
7. 7
   AutreThe residue was purified by flash chromatography
8. 8
   Autreto afford a solid matieral (1.3 g), which
9. 9
   workup.ADDITIONa mixture of starting material

Mode opératoire

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