(4-chloro-2-methylphenyl)boronic acid

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:

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: 4-iodoaniline (3.3 g, 15.0 mmol), (4-chloro-2-methylphenyl)boronic acid (3.3 g, 19.5 mmol), Pd(dppf)Cl2 (1.22 g, 1.5 mmol), and K2CO3 (4.1 g, 30 mmol) were dissolved in 1,4-dioxane (60 mL) and water (15 mL) and heated to 90° C. After 3 h the resulting mixture was diluted EtOAc and water and the layers were separated. The organic layer was dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound. EtOAc and water and the layers were separated The organic layer was dried (Na2SO4) concentrated purified via column chromatography

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

Procedure: 3-Chloro-4-iodoaniline (3.0 g, 11.8 mmol), (4-chloro-2-methylphenyl)boronic acid (2.4 g, 14.2 mmol), Pd(dppf)Cl2 (1.0 g, 1.2 mmol), and K2CO3 (3.3 g, 23.7 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 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

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

Procedure: Ethyl 3-(5-(2-(((4-iodophenyl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate (150 mg, 0.25 mmol), (4-chloro-2-methylphenyl)boronic acid (51 mg, 0.30 mmol), Pd(dppf)Cl2 (21 mg, 0.03 mmol), and K2CO3 (69 mg, 0.50 mmol) were dissolved in 1,4-dioxane (1.6 mL) and water (0.4 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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-(5-bromo-2-ethylphenyl)-4,4-dimethylcyclohexane-1,3-dione (0.194 g, 0.6 mmol), 2-methyl-4-chloro-phenylboronic acid (0.153 g, 0.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with dichloromethane 1:1) (80 mg, 0.098 mmol) and cesium fluoride (0.608 g, 4 mmol) are stirred together in 1,2-dimethoxyethane (4 ml) and the reaction mixture is heated at 80° C. overnight. The warm reaction mixture is filtered, washing the filter cake with 9:1 dichloromethane:methanol. The mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel to give 2-(4′-chloro-4-ethyl-2′-methylbiphen-3-yl)-4,4-dimethyl-cyclohexane-1,3-dione. The warm reaction mixture is filtered washing the filter cake with 9:1 dichloromethane The mixture is concentrated under reduced pressure the residue is purified by column chromatography on silica gel

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