2-Chloropyridine-5-boronic acid → 5-(6-Chloro-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

HRID 419801Notes

Reaction equation

HRID 419801 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](Br)[CH:13]=1)(=[O:3])[CH3:2].[Cl:27][C:28]1[N:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1>>[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@H:17]([O:23][C:24](=[O:26])[CH3:25])[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:31]2[CH:32]=[N:33][C:28]([Cl:27])=[CH:29][CH:30]=2)[CH:13]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 38450342-Chloropyridine-5-boronic acidHCID 441955025-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

Product 1

HCID 866326445-(6-Chloro-3-pyridinyl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

Procedure

By carrying out the operation analogously to example 1, starting from 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation IX, and 6-chloro-3-pyridineboronic acid, the desired product is obtained in the form of a white solid (yield=33%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-c5614e88caef4d0a9ef21e33cf48bc54
Source dataset
uspto-grants-2012_01
Patent number
US08093394B2

Reaction notes

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