4-Bromobenzoyl chloride → 4-bromophenyl 4-chloro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-indol-3-yl ketone
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[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1>>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:39]([C:38]1[CH:42]=[CH:43][C:35]([Br:34])=[CH:36][CH:37]=1)=[O:40])=[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]Participants
3
Procedure
4-Chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole obtained in Example 1-(3) and 4-bromobenzoyl chloride were treated in a manner similar to Example 2-(4) to give 4-bromophenyl 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indol-3-yl ketone as a colorless powder. APCI-Mass m/Z 664/666 (M+H). 1H-NMR (DMSO-d6) δ 1.69 (s, 3H), 1.97 (s, 3H), 1.98 (s, 3H), 2.04 (s, 3H), 4.11 (d, J=4.2 Hz, 2H), 4.30 (ddd, J=10.0, 4.3 and 4.2 Hz, 1H), 5.28 (t, J=9.8 Hz, 1H), 5.58 (t, J=9.6 Hz, 1H), 5.93 (t, J=9.4 Hz, 1H), 6.33 (d, J=9.0 Hz, 1H), 7.29 (d, J=7.5 Hz, 1H), 7.38 (t, J=8.0 Hz, 1H), 7.73-7.77 (m, 4H), 7.80 (d, J=8.2 Hz, 1H), 8.17 (s, 1H).
Sources & evidence
- ORD record
- ord-77111ce5cce4407c9d0af5aa772974a8
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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