Trifluoroacetic acid → 6-fluoro-5-methoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 1965330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1965330
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([C:20]4[CH:21]=[C:22]([O:26][CH3:27])[C:23]([F:25])=[CH:24][C:19]=4[O:18][CH2:17]3)[C:9]2=[O:28])C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[F:25][C:23]1[C:22]([O:26][CH3:27])=[CH:21][C:20]2[C:10]3([CH2:17][O:18][C:19]=2[CH:24]=1)[C:11]1[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:8][C:9]3=[O:28]

Komponenten

4

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 673566841'-(diphenylmethyl)-6-fluoro-5-methoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Produkt 1

HCID 673569246-fluoro-5-methoxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneAusbeute 93,3 %

Versuchsvorschrift

A suspended mixture of 1′-(diphenylmethyl)-6-fluoro-5-methoxyspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.49 g, 1.09 mmol), triethylsilane (0.23 g, 2.0 mmol) and trifluoroacetic acid (0.57 g, 5.0 mmol) was refluxed under nitrogen for 5 h. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The oily residue was sonicated with hexanes (10 mL) for 10 min and a solid product was filtered off to afford 6-fluoro-5-methoxyspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.29 g, 92%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ 9.28 (s, 1H), 7.37-6.91 (m, 4H), 6.74 (d, J=11.0 Hz, 1H), 6.39 (d, J=8.3 Hz, 1H), 4.82 (ABq, 2H), 3.68 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ180.0, 155.2, 154.9, 154.7, 151.9, 142.9, 142.7, 140.2, 132.1, 129.2, 124.1, 123.6, 122.7, 122.7, 110.4, 109.0, 108.9, 100.0, 99.7, 80.5, 58.8, 57.2; MS (ES+) m/z 285.8 (M+1).

Aufarbeitung

  1. temperaturewas refluxed under nitrogen for 5 h
  2. concentrationconcentrated under reduced pressure
  3. customThe oily residue was sonicated with hexanes (10 mL) for 10 min
  4. filtrationa solid product was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-0a0f6f30f7b54eba85fdbd1101615cd8
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415370B2

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