6-fluoro-5-methyl-1H-indole

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

Procedure: To a solution of cyano-(4-fluoro-5-methyl-2-nitrophenyl)acetic acid benzyl ester (1.54 g), acetic acid (7 mL) and water (7 mL) in ethanol (15 mL) was added 10% palladium-carbon (0.154 g) under an argon atmosphere. This reaction mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere. After water was added to this reaction mixture, hydrogen was exchanged by argon. The insoluble material was removed by filtration, and this filtrate was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0.536 g). The insoluble material was removed by filtration this filtrate was extracted with diethyl ether This organic layer was washed with brine dried over anhydrous magnesium sulfate filtered The solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)

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

Procedure: To a solution of cyano-(4-fluoro-5-methyl-2-nitrophenyl)acetic acid benzyl ester (1.54 g), acetic acid (7 mL) and water (7 mL) in ethanol (15 mL) was added 10% palladium-carbon (0.154 g) under an argon atmosphere. This reaction mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere. After water was added to this reaction mixture, hydrogen was exchanged by argon. The insoluble material was removed by filtration, and this filtrate was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0.536 g). The insoluble material was removed by filtration this filtrate was extracted with diethyl ether This organic layer was washed with brine dried over anhydrous magnesium sulfate filtered The solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)

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

Procedure: To a solution of cyano-(4-fluoro-5-methyl-2-nitrophenyl)acetic acid benzyl ester (1.54 g), acetic acid (7 mL) and water (7 mL) in ethanol (15 mL) was added 10% palladium-carbon (0.154 g) under an argon atmosphere. This reaction mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere. After water was added to this reaction mixture, hydrogen was exchanged by argon. The insoluble material was removed by filtration, and this filtrate was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0.536 g). The insoluble material was removed by filtration this filtrate was extracted with diethyl ether This organic layer was washed with brine dried over anhydrous magnesium sulfate filtered The solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)

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

Procedure: To a solution of cyano-(4-fluoro-5-methyl-2-nitrophenyl)acetic acid benzyl ester (1.54 g), acetic acid (7 mL) and water (7 mL) in ethanol (15 mL) was added 10% palladium-carbon (0.154 g) under an argon atmosphere. This reaction mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere. After water was added to this reaction mixture, hydrogen was exchanged by argon. The insoluble material was removed by filtration, and this filtrate was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0.536 g). The insoluble material was removed by filtration this filtrate was extracted with diethyl ether This organic layer was washed with brine dried over anhydrous magnesium sulfate filtered The solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)

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

Procedure: To a solution of cyano-(4-fluoro-5-methyl-2-nitrophenyl)acetic acid benzyl ester (1.54 g), acetic acid (7 mL) and water (7 mL) in ethanol (15 mL) was added 10% palladium-carbon (0.154 g) under an argon atmosphere. This reaction mixture was stirred at room temperature for 60 hours under a hydrogen atmosphere. After water was added to this reaction mixture, hydrogen was exchanged by argon. The insoluble material was removed by filtration, and this filtrate was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25) to give the title compound (0.536 g). The insoluble material was removed by filtration this filtrate was extracted with diethyl ether This organic layer was washed with brine dried over anhydrous magnesium sulfate filtered The solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)