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

HRID 419809Notes

Reaction equation

HRID 419809 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[CH:33]=[C:32](B(O)O)[CH:31]=[CH:30][N: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:32]2[CH:31]=[CH:30][N:29]=[C:28]([Cl:27])[CH:33]=2)[CH:13]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 51515952-Chloropyridine-4-boronic acidHCID 441955025-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylo-pyranoside

Product 1

HCID 866326485-(2-Chloro-4-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 2-chloro-4-pyridineboronic acid, the desired product is obtained in the form of an ecru solid (yield=55%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-29dca808ab934226a6bf8f7efee006e1
Source dataset
uspto-grants-2012_01
Patent number
US08093394B2

Reaction notes

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