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

HRID 544867Notes

Reaction equation

HRID 544867 reaction equation
[Cl: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>>[Br:34][C:35]1[S:39][C:38]([C:40]([C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])[N:6]([C@@H:11]3[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]3[O:13][C:14](=[O:16])[CH3:15])[CH:5]=2)=[O:41])=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 6057125-Bromothiophene-2-carbonyl chlorideHCID 670203794-Chloro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Product 1

HCID 671981034-chloro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-indol-3-yl 5-bromo-2-thienyl ketone

Procedure

4-Chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole obtained in Example 1-(3) and 5-bromothiophene-2-carbonyl chloride were treated in a manner similar to Example 2-(4) to give 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indol-3-yl 5-bromo-2-thienyl ketone as a yellow powder. APCI-Mass m/Z 670/672 (M+H). 1H-NMR (DMSO-d6) δ 1.67 (s, 3H), 1.97 (s, 3H), 1.99 (s, 3H), 2.05 (s, 3H), 4.11 (d, J=4.0 Hz, 2H), 4.30 (ddd, J=9.8, 4.2 and 3.9 Hz, 1H), 5.30 (t, J=9.8 Hz, 1H), 5.55 (t, J=9.6 Hz, 1H), 5.81 (t, J=9.3 Hz, 1H), 6.36 (d, J=9.0 Hz, 1H), 7.30 (d, J=7.5 Hz, 1H), 7.39 (t, J=8.0 Hz, 1H), 7.47 (d, J=3.9 Hz, 1H), 7.53 (d, J=4.0 Hz, 1H), 7.78 (d, J=8.3 Hz, 1H), 8.46 (s, 1H).

Sources & evidence

ORD record
ord-3fb627dc450f4f1e909e26f7b1181563
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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