2-Cyanopyridine-5-boronic acid → 3-(6-Cyano-3-pyridinyl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 907054Notes

Reaction equation

HRID 907054 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:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=1)(=[O:3])[CH3:2].[C:27]([C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)#[N:28]>>[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:13]=[CH:12][CH:11]=[C:10]([C:32]2[CH:33]=[N:34][C:29]([C:27]#[N:28])=[CH:30][CH:31]=2)[CH:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 547588122-Cyanopyridine-5-boronic acidHCID 673956003-bromophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 673982873-(6-Cyano-3-pyridinyl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 45%

Procedure

By carrying out the operation analogously to example 3, starting from 3-bromophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, obtained according to preparation VII, and 6-cyano-3-pyridineboronic acid, the expected product is obtained in the form of a white solid with a yield of 45%.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-1293ab9fabe548f485712bc8388bfe8b
Source dataset
uspto-grants-2011_09
Patent number
US08013010B2

Reaction notes

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