3,4-Dimethylphenol → 1-(diphenylmethyl)-5-fluoro-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one

HRID 2384966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384966
[O:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.CC1C=C(O)C=CC=1C.[C:20]1([CH:26]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:27]2[C:35]3[C:30](=[CH:31][C:32]([F:36])=[CH:33][CH:34]=3)[C:29](=[O:37])[C:28]2=[O:38])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(=O)C2=O)C=CC=CC=1>>[C:39]1([CH:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:27]2[C:35]3[C:30](=[CH:31][C:32]([F:36])=[CH:33][CH:34]=3)[C:29]([OH:37])([C:8]3[C:7]([OH:10])=[CH:6][C:5]4[O:1][CH2:2][CH2:3][C:4]=4[CH:9]=3)[C:28]2=[O:38])[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Komponenten

5

Edukt 4

HCID 72493,4-DimethylphenolHCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 122365402,3-Dihydro-1-benzofuran-6-olHCID 673565261-(diphenylmethyl)-5-fluoro-1H-indole-2,3-dione

Produkt 1

HCID 685987651-(diphenylmethyl)-5-fluoro-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one

Versuchsvorschrift

Following the procedure as described in PREPARATION 6A, and making non-critical variations using 2,3-dihydrobenzofuran-6-ol to replace 3,4-dimethylphenol, and 1-(diphenylmethyl)-5-fluoro-1H-indole-2,3-dione to replace 1-(diphenylmethyl)-1H-indole-2,3-dione, 1-(diphenylmethyl)-5-fluoro-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one was obtained (99%): 1H NMR (300 MHz, CDCl3) δ 8.94 (s, 1H), 7.36-7.19 (m, 11H), 6.94 (s, 1H), 6.82-6.75 (m, 1H), 6.63 (s, 1H), 6.48-6.38 (m, 2H), 4.53 (t, J=9.0 Hz, 2H), 4.38 (br s, 1H), 3.06-3.00 (m, 2H); MS (ES+) m/z 466.4 (M−1).

Quellen und Nachweise

ORD-Eintrag
ord-97050e513fc64ad9af5f1c84099eb612
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263606B2

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