(2-Hydroxy-5-methylphenyl)boronic acid → 6-(2-Hydroxy-5-methoxyphenyl)-6'-(2-hydroxy-5-methylphenyl)-2,2'-bipyridine

HRID 1263591Notes

Reaction equation

HRID 1263591 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=3[OH:22])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[OH:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=1B(O)O>CS(C)=O>[OH:22][C:15]1[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=1[C:10]1[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:25]3[CH:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:24]=3[OH:23])[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 18617005(2-Hydroxy-5-methylphenyl)boronic acidHCID 1358542856-Bromo-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 1354628376-(2-Hydroxy-5-methoxyphenyl)-6'-(2-hydroxy-5-methylphenyl)-2,2'-bipyridineYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-(2-Hydroxy-5-methoxyphenyl)-6′-(2-hydroxy-5-methylphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine and 2-hydroxy-5-methylphenylboronic acid in 50% yield using method F; δH [2H6]]-DMSO 13.27,(1H, b), 12.64,(1H, b), 8.37,(1H, d), 8.33,(1H, d), 8.21,(2H, t), 8.14,(2H, d), 7.93,(1H, s), 7.64,(1H, s), 7.17,(1H, d), 7.00,(1H, d), 6.93,(1H, d), 6.89,(1H, d), 3.82,(3H, s), 2.34,(3H, s).

Sources & evidence

ORD record
ord-e066260c20074b0596d3a4630ad58f09
Source dataset
uspto-grants-2003_04
Patent number
US06541490B1

Reaction notes

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