1-Benzofuran-5-carbonyl chloride → 3-(Benzo[b]furan-5-yl-methyl)-4-bromo-1-(beta-D-glucopyranosyl)-indole

HRID 544905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544905
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][O:30]C(=O)C)[C@@H:22]([O:23]C(=O)C)[C@H:17]([O:18]C(=O)C)[C@H:12]1[O:13]C(=O)C.[O:34]1[CH:38]=[CH:37][C:36]2[CH:39]=[C:40]([C:43](Cl)=O)[CH:41]=[CH:42][C:35]1=2>>[O:34]1[CH:38]=[CH:37][C:36]2[CH:39]=[C:40]([CH2:43][C:4]3[C:3]4[C:7](=[CH:8][CH:9]=[CH:10][C:2]=4[Br:1])[N:6]([C@@H:11]4[O:28][C@H:27]([CH2:29][OH:30])[C@@H:22]([OH:23])[C@H:17]([OH:18])[C@H:12]4[OH:13])[CH:5]=3)[CH:41]=[CH:42][C:35]1=2

Komponenten

3

Edukt 2

HCID 27762681-Benzofuran-5-carbonyl chlorideHCID 671978654-bromo-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Produkt 1

HCID 671989283-(Benzo[b]furan-5-yl-methyl)-4-bromo-1-(beta-D-glucopyranosyl)-indole

Versuchsvorschrift

The titled compound was prepared from 4-bromo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 22-(1) and benzo[b]furan-5-carbonyl chloride in a manner similar to Example 27 as a colorless powder. APCI-Mass m/Z 488/490 (M+H). 1H-NMR (DMSO-d6) δ 3.23 (td, J=9.1, 5.5 Hz, 1H), 3.37-3.47 (m, 3H), 3.61-3.69 (m, 2H), 4.39 (s, 2H), 4.53 (t, J=5.5 Hz, 1H), 5.09 (d, J=5.3 Hz, 1H), 5.15 (d, J=5.0 Hz, 1H), 5.22 (d, J=5.9 Hz, 1H), 5.40 (d, J=9.2 Hz, 1H), 6.87 (d, J=1.4 Hz, 1H), 7.04 (t, J=7.9 Hz, 1H), 7.21 (m, 2H), 7.25 (s, 1H), 7.43 (s, 1H), 7.49 (d, J=8.5 Hz, 1H), 7.60 (d, J=8.2 Hz, 1H), 7.93 (d, J=2.1 Hz, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-c292e9d0a96c4710982699107b982479
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935674B2

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