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

HRID 419805Notes

Reaction equation

HRID 419805 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][C:11](Br)=[CH:12][CH:13]=1)(=[O:3])[CH3:2].[Cl:27][C:28]1[C:33](B(O)O)=[CH:32][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][C:11]([C:33]2[C:28]([Cl:27])=[N:29][CH:30]=[CH:31][CH:32]=2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 2762704(2-Chloropyridin-3-yl)boronic acidHCID 866250296-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 866326466-(2-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 6-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation IV, and 2-chloro-3-pyridineboronic acid, the desired product is obtained in the form of an ecru solid (yield=43%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-ac8a6589eefe4117a1a190abd297205a
Source dataset
uspto-grants-2012_01
Patent number
US08093394B2

Reaction notes

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