(2-Hydroxy-3,4-dimethylphenyl)boronic acid → 6-(3,4-Dimethyl-2-hydroxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

HRID 566924Notes

Reaction equation

HRID 566924 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]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=3[OH:21])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:22][C:23]1[C:24]([OH:33])=[C:25](B(O)O)[CH:26]=[CH:27][C:28]=1[CH3:29]>>[CH3:22][C:23]1[C:24]([OH:33])=[C:25]([C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=4[OH:21])[N:9]=3)[CH:5]=[CH:4][CH:3]=2)[CH:26]=[CH:27][C:28]=1[CH3:29]

Participants

3

Reactant 2

HCID 18616950(2-Hydroxy-3,4-dimethylphenyl)boronic acidHCID 1358542886-Bromo-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

Product 1

HCID 1354628356-(3,4-Dimethyl-2-hydroxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridineYield 54%

Procedure

6-(3,4-Dimethyl-2-hydroxyphenyl)-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine and 3,4-dimethyl-2-hydroxyphenylboronic acid in 54% yield using method F; δH [2H6]-DMSO 13.40,(1H, b), 8.32,(2H, d), 8.24,(2H, m), 8.14-8.00,(3H, m), 7.86,(1H, d), 6.81,(3H, m), 2.33,(3H, s), 2.30,(3H, s), 2.19,(3H, s).

Sources & evidence

ORD record
ord-57ae0679381541aeb5b86e76eabf7b8e
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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