4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 66607925, compound

HRID 1625762Notes

Reaction equation

HRID 1625762 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH2:31][C:32]2[S:33][C:34](Br)=[CH:35][CH:36]=2)[CH:25]=1)(=[O:3])[CH3:2].CC1(C)C(C)(C)OB([C:46]2[CH:52]=[CH:51][C:49]([NH2:50])=[CH:48][CH:47]=2)O1>>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH2:31][C:32]2[S:33][C:34]([C:46]3[CH:52]=[CH:51][C:49]([NH2:50])=[CH:48][CH:47]=3)=[CH:35][CH:36]=2)[CH:25]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 600412891-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl)-3-(5bromo-2-thienylmethyl)-4-chlorobenzene

Product 1

HCID 66607925HCID 66607925, compound

Procedure

1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-3-(5-bromo-2-thienylmethyl)-4-chlorobenzene obtained in Example 128-(4) and 4-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)aniline were treated in a manner similar to Example 168-(1) to give 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-(5-(4-aminophenyl)-2-thienylmethyl)-4-chlorobenzene as pale yellow powder. APCI-Mass m/Z 630/632 (M+H).

Sources & evidence

ORD record
ord-890f9f6f92444d788c538701ac33af94
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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