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

HRID 566930Notes

Reaction equation

HRID 566930 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][CH:17]=[C:16]([O:20][CH3:21])[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]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[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 1358542866-Bromo-6'-(2-hydroxy-3-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 1354628626-(3,4-Dimethyl-2-hydroxyphenyl)-6'-(2-hydroxy-3-methoxyphenyl)-2,2'-bipyridineYield 11%

Procedure

6-(3,4-Dimethyl-2-hydroxyphenyl)-6′-(2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine and 3,4-dimethyl-2-hydroxyphenylboronic acid in 11% yield using method F; δH [2H6]-DMSO 13.32,(1H, s), 8.38-8.22,(4H, m), 8.14,(1H, d), 8.10,(1H, d), 7.88,(1H, d), 7.72,(1H, d), 7.10,(1H, d), 6.94,(1H, t), 6.82,(1H, d), 3.84,(3H, s), 2.31,(3H, s), 2.20,(3H, s); MS 339 (MH)+; HPLC retention time (system 1) 4.39 minutes.

Workup

  1. customHPLC retention time (system 1) 4.39 minutes

Sources & evidence

ORD record
ord-d40ad5aa47504e679e4fffeb52656d01
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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