(2-Hydroxyphenyl)boronic acid → 6-(2-Hydroxyphenyl)-6'-(2-hydroxy-3-methoxyphenyl)-2,2'-bipyridine

HRID 566926Notes

Reaction equation

HRID 566926 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][CH:27]=[CH:26][C:25]=1B(O)O>>[OH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[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

Participants

3

Reactant 2

HCID 2773454(2-Hydroxyphenyl)boronic acidHCID 1358542866-Bromo-6'-(2-hydroxy-3-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 1354560076-(2-Hydroxyphenyl)-6'-(2-hydroxy-3-methoxyphenyl)-2,2'-bipyridineYield 39%

Procedure

6-(2-Hydroxyphenyl)-6′-(2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine and 2-hydroxyphenyl boronic acid in 39% yield using method F; δH [2H6]-DMSO 13.48,(1H, b), 13.38,(1H, b), 8.33,(2H, m), 8.23, (2H, t), 8.17,(2H, d), 8.13,(1H, d), 7.70,(2H, d), 7.37,(1H, t), 7.09,(1H, d), 7.02,(1H, d), 6.94,(1H, t), 3.84,(3H, s); MS 371 (MH)+; HPLC retention time (system 1) 4.03 minutes.

Workup

  1. customHPLC retention time (system 1) 4.03 minutes

Sources & evidence

ORD record
ord-f236adab9c7f4faca3ef30f5277b7cc4
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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