(2-amino-4-chlorophenyl)-(4-fluorophenyl)methanone

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

Procedure: To solution of 5-chloro-2-(4-fluorobenzoyl)aniline (5 g) in 6M aqueous HCl (25 ml) was added a solution of NaNO2 (2.5 g) in water (5 ml) at 0°-5° C. under stirring during 15 min. After stirring for further 0.5 h at 0° C. a solution of SnCl2 (20 g) in conc. aqueous HCl (25 ml) was added. The reaction mixture was allowed to heat to room temperature and after 0.5 h the precipitate was filtered off and suspended in 2 N aqueous NaOH. The suspension was filtered and dichloromethane was added to the precipitate. The thus obtained solution was washed with brine and dried (MgSO4). Evaporation of the solvents afforded the title compound (2.5 g) as an oil which was used without further purification. In a corresponding manner the following indazole derivative was prepared: 3-(4-Fluorophenyl)-5-trifluoromethyl-1H-indazole 25b, (oil) was added was filtered off The suspension was filtered dichloromethane was added to the precipitate The thus obtained solution was washed with brine dried (MgSO4) Evaporation of the solvents

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

Procedure: To solution of 5-chloro-2-(4-fluorobenzoyl)aniline (5 g) in 6M aqueous HCl (25 ml) was added a solution of NaNO2 (2.5 g) in water (5 ml) at 0°-5° C. under stirring during 15 min. After stirring for further 0.5 h at 0° C. a solution of SnCl2 (20 g) in conc. aqueous HCl (25 ml) was added. The reaction mixture was allowed to heat to room temperature and after 0.5 h the precipitate was filtered off and suspended in 2 N aqueous NaOH. The suspension was filtered and dichloromethane was added to the precipitate. The thus obtained solution was washed with brine and dried (MgSO4). Evaporation of the solvents afforded the title compound (2.5 g) as an oil which was used without further purification. In a corresponding manner the following indazole derivative was prepared: 3-(4-Fluorophenyl)-5-trifluoromethyl-1H-indazole 25b, (oil) was added was filtered off The suspension was filtered dichloromethane was added to the precipitate The thus obtained solution was washed with brine dried (MgSO4) Evaporation of the solvents

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

Procedure: To solution of 5-chloro-2-(4-fluorobenzoyl)aniline (5 g) in 6M aqueous HCl (25 ml) was added a solution of NaNO2 (2.5 g) in water (5 ml) at 0°-5° C. under stirring during 15 min. After stirring for further 0.5 h at 0° C. a solution of SnCl2 (20 g) in conc. aqueous HCl (25 ml) was added. The reaction mixture was allowed to heat to room temperature and after 0.5 h the precipitate was filtered off and suspended in 2 N aqueous NaOH. The suspension was filtered and dichloromethane was added to the precipitate. The thus obtained solution was washed with brine and dried (MgSO4). Evaporation of the solvents afforded the title compound (2.5 g) as an oil which was used without further purification. In a corresponding manner the following indazole derivative was prepared: 3-(4-Fluorophenyl)-5-trifluoromethyl-1H-indazole 25b, (oil) was added was filtered off The suspension was filtered dichloromethane was added to the precipitate The thus obtained solution was washed with brine dried (MgSO4) Evaporation of the solvents

Conditions: temp:-65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 54.0 g (0.216 mole) of 4-chloro-4'-fluoro-2-aminobenzophenone in 700 ml of methylene chloride was cooled to -65° C. and 30.5 g (0.227 mol) of ethyl-2-methylthioacetate was added. Twenty six (26) g (0.227 mol) of 95% tertiary butoxy chloride was added dropwise under stirring over a 20 minute period while maintaining the temperature of the solution at -65° C. The resulting light brown yellow solution was stirred at -70° C. for one hour and 25 g (0.25 mol) of triethylamine was added to the solution. This mixture was allowed to warm to room temperature and 400 ml of 3N HCl was added to the mixture. The resulting mixture was heated at reflux temperature under vigorous stirring for 2 hrs. The resulting organic phase was separated, washed with 100 ml of water and dried. The methylene chloride was evaporated and the residue triturated with diethyloxide. The resulting solid was collected by filtration, washed and dried to give 35.1 g of product. The product was crystallized to give 31.1 g (43%) of the titled compound as off-white crystals, mp. 202°-204° C. The resulting light brown yellow solution was stirred at -70° C. for one hour to warm to room temperature The resulting mixture was heated at reflux temperature under vigorous stirring for 2 hrs The resulting organic phase was separated washed with 100 ml of water dried The methylene chloride was evaporated the residue triturated with diethyloxide The resulting solid was collected by filtration washed dried

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

Procedure: To solution of 5-chloro-2-(4-fluorobenzoyl)aniline (5 g) in 6M aqueous HCl (25 ml) was added a solution of NaNO2 (2.5 g) in water (5 ml) at 0°-5° C. under stirring during 15 min. After stirring for further 0.5 h at 0° C. a solution of SnCl2 (20 g) in conc. aqueous HCl (25 ml) was added. The reaction mixture was allowed to heat to room temperature and after 0.5 h the precipitate was filtered off and suspended in 2 N aqueous NaOH. The suspension was filtered and dichloromethane was added to the precipitate. The thus obtained solution was washed with brine and dried (MgSO4). Evaporation of the solvents afforded the title compound (2.5 g) as an oil which was used without further purification. In a corresponding manner the following indazole derivative was prepared: 3-(4-Fluorophenyl)-5-trifluoromethyl-1H-indazole 25b, (oil) was added was filtered off The suspension was filtered dichloromethane was added to the precipitate The thus obtained solution was washed with brine dried (MgSO4) Evaporation of the solvents