4-Bromobenzoyl chloride → 4-Bromo-3-(4-bromophenylmethyl)-1-(beta-D-glucopyranosyl)indole
Reaction equation
[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.[Br:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=O)=[CH:37][CH:36]=1>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:39][C:38]1[CH:42]=[CH:43][C:35]([Br:34])=[CH:36][CH:37]=1)=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][OH:30])[C@@H:22]([OH:23])[C@H:17]([OH:18])[C@H:12]1[OH:13]Participants
3
Procedure
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 4-bromobenzoyl chloride in a manner similar to Example 3 as a colorless powder. APCI-Mass m/Z 526/528/530 (M+H). 1H-NMR (DMSO-d6) δ 3.20-3.48 (m, 4H), 3.66 (m, 2H), 4.27 (s, 2H), 4.54 (t, J=5.4 Hz, 1H), 5.10 (d, J=5.3 Hz, 1H), 5.17 (d, J=5.0 Hz, 1H), 5.23 (d, J=5.8 Hz, 1H), 5.41 (d, J=9.0 Hz, 1H), 7.04 (t, J=7.9 Hz, 1H), 7.16 (d, J=8.3 Hz, 2H), 7.21 (d, J=7.5 Hz, 1H), 7.33 (s, 1H), 7.45 (d, J=8.3 Hz, 2H), 7.60 (d, J=8.2 Hz, 1H).
Sources & evidence
- ORD record
- ord-2afcb7753060432c887ab1aa58da7970
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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