4-bromo-1,1,1-trifluoro-2-(trifluoromethyl)butane

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

Procedure: 1.89 g (8.07 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Example 87A were initially charged in 60 ml of DMF, 7.89 g (24.2 mmol) of caesium carbonate and 2.30 g (8.88 mmol) of 4,4,4-trifluoro-3-(trifluoromethyl)butyl bromide were added and the reaction mixture was stirred at RT for 90 min. 60 ml of water were then added, the precipitated solid was filtered off and the filter residue was washed with 100 ml of water and twice with 20 ml of tert-butyl methyl ether. The precipitate obtained from the filtrate was filtered off and washed with mother liquor. Both filter residues were taken up in 50 ml of ethyl acetate. The solution was concentrated on a rotary evaporator and the residue was dried under reduced pressure overnight. This gave 2.25 g of the target compound (95% pure, 64% of theory). the precipitated solid was filtered off the filter residue was washed with 100 ml of water and twice with 20 ml of tert-butyl methyl ether The precipitate obtained from the filtrate was filtered off washed with mother liquor The solution was concentrated on a rotary evaporator the residue was dried under reduced pressure overnight

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

Procedure: 1.89 g (8.07 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Example 87A were initially charged in 60 ml of DMF, 7.89 g (24.2 mmol) of caesium carbonate and 2.30 g (8.88 mmol) of 4,4,4-trifluoro-3-(trifluoromethyl)butyl bromide were added and the reaction mixture was stirred at RT for 90 min. 60 ml of water were then added, the precipitated solid was filtered off and the filter residue was washed with 100 ml of water and twice with 20 ml of tert-butyl methyl ether. The precipitate obtained from the filtrate was filtered off and washed with mother liquor. Both filter residues were taken up in 50 ml of ethyl acetate. The solution was concentrated on a rotary evaporator and the residue was dried under reduced pressure overnight. This gave 2.25 g of the target compound (95% pure, 64% of theory). the precipitated solid was filtered off the filter residue was washed with 100 ml of water and twice with 20 ml of tert-butyl methyl ether The precipitate obtained from the filtrate was filtered off washed with mother liquor The solution was concentrated on a rotary evaporator the residue was dried under reduced pressure overnight

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

Procedure: A solution of 40 mg (0.10 mmol) of rac-[1-{[7-hydroxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carbonyl)amino]}-1-methylbutyl)carbamic acid tert-butyl ester (Example 141A) in 1 ml of DMF was admixed with 65 mg (0.2 mmol) of caesium carbonate and 78 mg (0.3 mmol) of 4-bromo-1,1,1-trifluoro-2-(trifluoromethyl)butane (CAS: 203303-02-0). The reaction mixture was stirred at room temperature for 18 hours. The solvent was evaporated off under reduced pressure. The residue was partitioned between dichloromethane and water, the phases were separated and the organic phase was concentrated under reduced pressure, which gave 55 mg (51% yield, 54% pure) of the target compound, which was used in the next step without further purification. The solvent was evaporated off under reduced pressure The residue was partitioned between dichloromethane and water the phases were separated the organic phase was concentrated under reduced pressure, which gave 55 mg (51% yield, 54% pure) of the target compound, which was used in the next step without further purification