4-Acetylbenzenesulphonamide → 4-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide

HRID 10707

Reaktionsgleichung

Reaktionsgleichung von HRID 10707
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[C:23]1[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:30]=1)[CH:28]=O>>[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[C:23]1[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27](/[CH:28]=[CH:2]/[C:1]([C:4]2[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=2)=[O:3])[CH:30]=1

Komponenten

3

Edukt 2

HCID 740654-AcetylbenzenesulphonamideHCID 161156215-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

Produkt 1

HCID 210416274-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamideAusbeute 70 %

Versuchsvorschrift

The title compound was prepared by condensing 4-acetyl-benzenesulfonamide (Ex-26A) and 5-(1H-indol-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-61A) in a similar manner as described in Ex-22. Red solid, 70% yield, mp 185–187° C. 1H-NMR (DMSO-d6) δ 11.15 (br, s, 1H), 8.33 (s, 1H), 8.24 (d, J=8 Hz, 2H), 8.07 (d, J=15 Hz, 1H), 7.98 (d, J=8 Hz, 2H), 7.80 (d, J=15 Hz, 1H), 7.41–7.55 (m, 4H), 7.03–7.08 (m, 1H), 6.93–6.99 (m, 2H), 6.83 (s, 1H), 4.04 (s, 3H), 3.99 (s, 3H). MS m/z=463 ([M+H]+). HRMS (ES+) Calcd. for C25H22N2O5S: 463.1327. Found: 463.1316.

Quellen und Nachweise

ORD-Eintrag
ord-3b7afba2aacb43fd9ab8004bc2469531
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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