Acetic Acid → 6-fluoro-5-methyl-1H-indole
Reaction equation
C(OC(=O)[CH:10]([C:22]#[N:23])[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([F:18])=[CH:13][C:12]=1[N+]([O-])=O)C1C=CC=CC=1.C(O)(=O)C.O.[H][H]>C(O)C.[C].[Pd]>[F:18][C:14]1[CH:13]=[C:12]2[C:11]([CH:10]=[CH:22][NH:23]2)=[CH:16][C:15]=1[CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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).
Workup
- customThe insoluble material was removed by filtration
- extractionthis filtrate was extracted with diethyl ether
- washThis organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe solvent was removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=75/25)
Sources & evidence
- ORD record
- ord-1a0d5c7ec0a949f59f0b2a57aeecc8a1
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08829040B2
Reaction notes
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