1-Bromo-4-(difluoromethyl)benzene → 4-chloro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indol-3-yl 4-(difluoromethyl)phenyl methanol
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:34]=[O:35])=[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[C:37]1[CH:42]=[CH:41][C:40]([CH:43]([F:45])[F:44])=[CH:39][CH:38]=1>>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:34]([C:37]1[CH:42]=[CH:41][C:40]([CH:43]([F:45])[F:44])=[CH:39][CH:38]=1)[OH:35])=[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-3-carboxaldehyde obtained in Example 29-(1) and 1-bromo-4-difluoromethylbenzene were treated in a manner similar to Example 25-(2) to give crude 4-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indol-3-yl 4-(difluoromethyl)phenyl methanol, which was used in the subsequent step without further purification.
Sources & evidence
- ORD record
- ord-4c882707616a441b9d8942a85e7b5f70
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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