(2-Hydroxy-5-methylphenyl)boronic acid → 6-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-5-methylphenyl)-2,2'-bipyridine

HRID 566931Notes

Reaction equation

HRID 566931 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.[OH:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=1B(O)O>>[OH:22][C:15]1[C:16]([O:20][CH3:21])=[CH:17][CH:18]=[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

3

Reactant 2

HCID 18617005(2-Hydroxy-5-methylphenyl)boronic acidHCID 1358542866-Bromo-6'-(2-hydroxy-3-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 1354309206-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-5-methylphenyl)-2,2'-bipyridineYield 20%

Procedure

6-(2-Hydroxy-3-methoxyphenyl)-6′-(2-hydroxy-5-methylphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine and 2-hydroxy-5-methylphenylboronic acid in 20% yield using method F; δH [2H6]-DMSO 13.57,(1H, b), 13.09,(1H, b), 8.33,(2H, t), 8.24,(2H, m), 8.15,(2H, m), 7.95,(1H, s), 7.70,(1H, d), 7.18,(1H, d), 7.10,(1H, d), 6.91,(2H, m), 3.84,)3H, s), 2.35,(3H, s); MS 385 (MH)+; HPLC retention time (system 1) 4.17 minutes.

Workup

  1. customHPLC retention time (system 1) 4.17 minutes

Sources & evidence

ORD record
ord-86372f6dd7b94d0e8fb55b986b8fe300
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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