5-Bromothiophene-2-carbonyl chloride → 5-bromo-2-thienyl 4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indol-3-yl ketone

HRID 544907

Reaktionsgleichung

Reaktionsgleichung von HRID 544907
[CH3:1][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:31](=[O:33])[CH3:32])[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]1[O:13][C:14](=[O:16])[CH3:15].[Br:34][C:35]1[S:39][C:38]([C:40](Cl)=[O:41])=[CH:37][CH:36]=1>>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:40]([C:38]1[S:39][C:35]([Br:34])=[CH:36][CH:37]=1)=[O:41])=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]1[O:13][C:14](=[O:16])[CH3:15]

Komponenten

3

Edukt 2

HCID 6057125-Bromothiophene-2-carbonyl chlorideHCID 671958784-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Produkt 1

HCID 671990345-bromo-2-thienyl 4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indol-3-yl ketone

Versuchsvorschrift

4-Methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole obtained in Example 23-(1) and 5-bromothiophene-2-carbonyl chloride were treated in a manner similar to Example 21-(1) to give 5-bromo-2-thienyl 4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indol-3-yl ketone as a yellow powder. APCI-Mass m/Z 650/652 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-27c81cb2c2714add894e9426b9ee003f
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935674B2

Verknüpfte Notizen

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