1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-acetyl-5-(2-aminopropyl)indoline-7-carbonitrile (1.37 g) and 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene (1.50 g) in ethanol (6 ml) was added sodium bicarbonate (0.47 g), and the mixture was reacted in a sealed tube at 95° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent, and recrystallized from diethyl ether-hexane to give 1.30 g of 1-acetyl-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carbonitrile melting at 64°-65° C. the mixture was reacted in a sealed tube at 95° C. for 12 hours The reaction mixture was concentrated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent recrystallized from diethyl ether-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-acetyl-5-(2-aminopropyl)indoline-7-carbonitrile (1.37 g) and 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene (1.50 g) in ethanol (6 ml) was added sodium bicarbonate (0.47 g), and the mixture was reacted in a sealed tube at 95° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent, and recrystallized from diethyl ether-hexane to give 1.30 g of 1-acetyl-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carbonitrile melting at 64°-65° C. the mixture was reacted in a sealed tube at 95° C. for 12 hours The reaction mixture was concentrated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent recrystallized from diethyl ether-hexane

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an aqueous solution (15 ml) of sodium hydroxide (0.63 g) were added 2-(2,2,2-trifluoroethoxy)phenol (2.85 g) and 1,2-dibromoethane (1.68 ml), and the mixture was reacted with stirring at 120° C. for 8 hours. To the reaction mixture was added concentrated hydrochloric acid (1.3 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (5/1) as eluent to give 1.78 g of 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene as an oil the mixture was reacted the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (5/1) as eluent

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an aqueous solution (15 ml) of sodium hydroxide (0.63 g) were added 2-(2,2,2-trifluoroethoxy)phenol (2.85 g) and 1,2-dibromoethane (1.68 ml), and the mixture was reacted with stirring at 120° C. for 8 hours. To the reaction mixture was added concentrated hydrochloric acid (1.3 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (5/1) as eluent to give 1.78 g of 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene as an oil the mixture was reacted the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (5/1) as eluent

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-acetyl-5-(2-aminopropyl)indoline-7-carbonitrile (1.37 g) and 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene (1.50 g) in ethanol (6 ml) was added sodium bicarbonate (0.47 g), and the mixture was reacted in a sealed tube at 95° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent, and recrystallized from diethyl ether-hexane to give 1.30 g of 1-acetyl-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carbonitrile melting at 64°-65° C. the mixture was reacted in a sealed tube at 95° C. for 12 hours The reaction mixture was concentrated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent recrystallized from diethyl ether-hexane

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an aqueous solution (15 ml) of sodium hydroxide (0.63 g) were added 2-(2,2,2-trifluoroethoxy)phenol (2.85 g) and 1,2-dibromoethane (1.68 ml), and the mixture was reacted with stirring at 120° C. for 8 hours. To the reaction mixture was added concentrated hydrochloric acid (1.3 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (5/1) as eluent to give 1.78 g of 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene as an oil the mixture was reacted the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (5/1) as eluent

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-acetyl-5-(2-aminopropyl)indoline-7-carbonitrile (1.37 g) and 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene (1.50 g) in ethanol (6 ml) was added sodium bicarbonate (0.47 g), and the mixture was reacted in a sealed tube at 95° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent, and recrystallized from diethyl ether-hexane to give 1.30 g of 1-acetyl-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carbonitrile melting at 64°-65° C. the mixture was reacted in a sealed tube at 95° C. for 12 hours The reaction mixture was concentrated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent recrystallized from diethyl ether-hexane

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To an aqueous solution (15 ml) of sodium hydroxide (0.63 g) were added 2-(2,2,2-trifluoroethoxy)phenol (2.85 g) and 1,2-dibromoethane (1.68 ml), and the mixture was reacted with stirring at 120° C. for 8 hours. To the reaction mixture was added concentrated hydrochloric acid (1.3 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (5/1) as eluent to give 1.78 g of 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene as an oil the mixture was reacted the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (5/1) as eluent