Trifluoroacetic acid → 7-[1-(diphenylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-6-hydroxy-4-methyl-2H-1,4-benzoxazin-3(4H)-one

HRID 1407402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1407402
[C:1]1([CH:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:18]3[C:29]([OH:30])=[CH:28][C:21]4[N:22]([CH3:27])[C:23](=[O:26])[CH2:24][O:25][C:20]=4[CH:19]=3)(O)[C:9]2=[O:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[C:32]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:18]3[C:29]([OH:30])=[CH:28][C:21]4[N:22]([CH3:27])[C:23](=[O:26])[CH2:24][O:25][C:20]=4[CH:19]=3)[C:9]2=[O:31])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

4

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 685977597-(1-benzhydryl-3-hydroxy-2-oxoindolin-3-yl)-6-hydroxy-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Produkt 1

HCID 686010007-[1-(diphenylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-6-hydroxy-4-methyl-2H-1,4-benzoxazin-3(4H)-oneAusbeute 71 %

Versuchsvorschrift

To a solution of 7-[1-(diphenylmethyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl]-6-hydroxy-4-methyl-2H-1,4-benzoxazin-3(4H)-one (4.0 g, 8.1 mmol) in trifluoroacetic acid (1.8 mL, 24.4 mmol) was added triethylsilane (3.9 mL, 24.4 mmol) and the reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography with ethyl acetate in hexanes (10 to 100% gradient) to afford 7-[1-(diphenylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-6-hydroxy-4-methyl-2H-1,4-benzoxazin-3(4H)-one (2.66 g, 71%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ9.53 (s, 1H), 7.44-7.28 (m, 10H), 6.99-6.95 (m, 3H), 6.89-6.84 (m, 2H), 6.54 (s, 1H), 6.40 (m, 1H), 4.90 (s, 1H), 4.57 (s, 2H), 3.21 (s, 3H); MS (ES+) m/z 477.0 (M+1).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was purified by column chromatography with ethyl acetate in hexanes (10 to 100% gradient)

Quellen und Nachweise

ORD-Eintrag
ord-a11f4f24fee14f34b404e256ee0098ab
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916580B2

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