4-Iodobenzoyl chloride → 4-Chloro-5-fluoro-3-(4-iodophenylmethyl)-1-(beta-D-gluco-pyranosyl)indole
Reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C@@H:12]1[O:29][C@H:28]([CH2:30][O:31]C(=O)C)[C@@H:23]([O:24]C(=O)C)[C@H:18]([O:19]C(=O)C)[C@H:13]1[O:14]C(=O)C.[I:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=O)=[CH:38][CH:37]=1>>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:40][C:39]1[CH:43]=[CH:44][C:36]([I:35])=[CH:37][CH:38]=1)=[CH:5][N:6]2[C@@H:12]1[O:29][C@H:28]([CH2:30][OH:31])[C@@H:23]([OH:24])[C@H:18]([OH:19])[C@H:13]1[OH:14]Participants
3
Procedure
4-Chloro-5-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl)indole obtained in Example 34-(3) and 4-Iodobenzoyl chloride were treated in a manner similar to Example 3 to give the titled compound as a colorless powder. APCI-Mass m/Z 548/550 (M+H). 1H-NMR (DMSO-d6) δ 3.15-3.45 (m, 4H), 3.62 (m, 2H), 4.21 (s, 2H), 4.52-4.58 (br, 1H), 5.10-5.17 (br, 1H), 5.18-5.30 (br, 2H), 5.40 (d, J=9.0 Hz, 1H), 7.02 (d, J=8.2 Hz, 2H), 7.16 (t, J=9.3 Hz, 1H), 7.42 (s, 1H), 7.57 (dd, J=9.0, 4.0 Hz, 1H), 7.62 (d, J=8.3 Hz, 2H).
Sources & evidence
- ORD record
- ord-ee470d486f3c499aa6cb54421cbd2670
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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