4-Bromobenzoyl chloride → 3-(4-bromophenylmethyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

HRID 544909Notes

Reaction equation

HRID 544909 reaction equation
[CH3:1][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)=[CH:37][CH:36]=1>>[Br:34][C:35]1[CH:43]=[CH:42][C:38]([CH2:39][C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[CH3:1])[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)=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 671958784-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Product 1

HCID 671974083-(4-bromophenylmethyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Procedure

4-Methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole obtained in Example 23-(1) and 4-bromobenzoyl chloride were treated in a manner similar to Example 2-(4), (5) and 3-(3) to give 3-(4-bromophenylmethyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole as pale pink crystals. mp 190-192° C. APCI-Mass m/Z 630/632 (M+H).

Sources & evidence

ORD record
ord-6068cd3c2e4948e09414bc26e87ae291
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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