4-bromo-3-chloroaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described in Example 159 substituting 3-chloro-4-iodoaniline and (2-chloro-4-methoxyphenyl)boronic acid for 4-bromo-3-chloroaniline and (4-(trifluoromethyl)phenyl)boronic acid, respectively.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described in Example 159 substituting 4-bromo-3-methoxyaniline and (2-methyl-4-(trifluoromethyl)phenyl)boronic acid for 4-bromo-3-chloroaniline and (4-(trifluoromethyl)phenyl)boronic acid, respectively.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described in Example 159 substituting 4-bromo-3-methoxyaniline and (4-chloro-2-methylphenyl)boronic acid for 4-bromo-3-chloroaniline and (4-(trifluoromethyl)phenyl)boronic acid, respectively.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described in Example 159 substituting 4-bromoaniline and (2-chloro-4-(trifluoromethyl)phenyl)boronic acid for 4-bromo-3-chloroaniline and (4-(trifluoromethyl)phenyl)boronic acid, respectively.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described in Example 159 substituting 4-bromo-3,5-dichloroaniline and (4-chlorophenyl)boronic acid for 4-bromo-3-chloroaniline and (4-(trifluoromethyl)phenyl)boronic acid, respectively.

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-bromo-3-chloroaniline (2.1 g, 10.2 mmol), (4-(trifluoromethyl)phenyl)boronic acid (2.7 g, 14.2 mmol), Pd(dppf)Cl2 (744 mg, 1.0 mmol), 2M aqueous Na2CO3 (15.3 mL, 30.5 mmol) were dissolved in 1,4-dioxane (30 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, was diluted with EtOAc, washed with water and brine. The organic layer was dried (Na2SO4), concentrated and diethyl ether was added. The resulting precipitate was filtered and dried in vacuo to yield the title compound. After 16 h the resulting mixture was cooled to room temperature washed with water and brine The organic layer was dried (Na2SO4) concentrated diethyl ether was added The resulting precipitate was filtered dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-3-chloroaniline (3.0 g, 14.5 mmol), (2,4-dichlorophenyl)boronic acid (3.6 g, 18.9 mmol), Pd(dppf)Cl2 (1.2 g, 1.5 mmol), and K2CO3 (4.0 g, 29.1 mmol) were dissolved in 1,4-dioxane (60 mL) and water (15 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound. washed with water and brine dried (Na2SO4) dry