Reaktion #593362

ord-2e3d76ae270d4a529e4439bf1d4489a3

Reaktionsgleichung

CC(=O)N1CCc2c(F)cccc21
1-(4-fluoro-2,3-dihydro-indol-1-yl)-ethanone
Fc1cccc2[nH]ccc12
4-fluoroindole
O=S(=O)(O)O
H2SO4
O=[N+]([O-])O
HNO3
→
CC(=O)N1CCc2c1ccc([N+](=O)[O-])c2F
1-(4-fluoro-5-nitro-2,3-dihydro-indol-1-yl)-ethanone

Edukte

CC(=O)N1CCc2c(F)cccc21
1-(4-fluoro-2,3-dihydro-indol-1-yl)-ethanone
Fc1cccc2[nH]ccc12
4-fluoroindole
O=S(=O)(O)O
H2SO4
O=[N+]([O-])O
HNO3

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Treatment of 1-(4-fluoro-2,3-dihydro-indol-1-yl)-ethanone, prepared from 4-fluoroindole (See e.g., EP 0645385A1), with concentrated H2SO4 and fuming HNO3 in glacial acetic acid gave 1-(4-fluoro-5-nitro-2,3-dihydro-indol-1-yl)-ethanone. Deprotection of the acetyl group with Na2S in aqueous ethanol provided 4-fluoro-5-nitro-2,3-dihydro-1H-indole, which was treated with 2,3-dicyano-5,6-dichloro-parabenzoquinone (DDQ) to provide 4-fluoro-5-nitroindole. A subsequent hydrogenation over Pd/C gave 5-amino-4-fluoroindole.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07781591B2uspto-grants-2010_08