(2-Hydroxy-3,4-dimethylphenyl)boronic acid → 6-(3,4-Dimethyl-2-hydroxyphenyl)-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

HRID 1263589Notes

Reaction equation

HRID 1263589 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.[CH3:23][C:24]1[C:25]([OH:34])=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[CH3:30]>>[CH3:23][C:24]1[C:25]([OH:34])=[C:26]([C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=4[OH:22])[N:9]=3)[CH:5]=[CH:4][CH:3]=2)[CH:27]=[CH:28][C:29]=1[CH3:30]

Participants

3

Reactant 2

HCID 18616950(2-Hydroxy-3,4-dimethylphenyl)boronic acidHCID 1358542856-Bromo-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 1356734146-(3,4-Dimethyl-2-hydroxyphenyl)-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridineYield 50%

Procedure

6-(3,4-Dimethyl-2-hydroxyphenyl)-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine and 3,4-dimethyl-2-hydroxyphenylboronic acid in 50% yield using method F; δH [2H6]-DMSO 12.40,(1H, b), 8.38,(1H, d), 8.31,(1H, d), 8.28-8.20,(2H, m), 8.14,(1H, d), 8.09,(1H, d), 7.86,(1H, d), 7.66,(1H, s), 7.00,(1H, d), 6.94,(1H, d), 6.81,(1H, d), 3.82,(3H, s), 2.30,(3H, s), 2.19,(3H, s).

Sources & evidence

ORD record
ord-aafaf2540891427e846bbaca685e312e
Source dataset
uspto-grants-2003_04
Patent number
US06541490B1

Reaction notes

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