Trifluoroacetic acid → HCID 21268184, Verbindung

Reaktionsgleichung

[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH:18]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([SiH](CC)CC)C.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

Edukt 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane2×

HCID 212682696-Nitro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole

Produkt 1

HCID 21268184HCID 21268184, VerbindungAusbeute 67 %

Versuchsvorschrift

To a mixture of 2.4 gm (9.9 mMol) 6-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 10.0 mL trifluoroacetic acid were added 1.65 mL (10.4 mMol) triethylsilane. After an initial exotherm, the reaction was allowed to stir for 18 hours at ambient temperature. At this point an additional 0.5 mL triethylsilane were added and the reaction mixture stirred for 24 hours. The reaction mixture was then concentrated under reduced pressure. The residue was crystallized from ethanol to give 2.4 gm (67%) of the title compound.