(2-Hydroxyphenyl)boronic acid → 6-(2-Hydroxyphenyl)-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

HRID 566932Notes

Reaction equation

HRID 566932 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.[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]=[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

Participants

3

Reactant 2

HCID 2773454(2-Hydroxyphenyl)boronic acidHCID 1358542856-Bromo-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 1356734366-(2-Hydroxyphenyl)-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridineYield 66%

Procedure

6-(2-Hydroxyphenyl)-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine and 2-hydroxyphenylboronic acid in 66% yield using method F; δH [2H6]-DMSO 13.55,(1H, s), 12.57,(1H, s), 8.35,(2H, m), 8.27-8.10,(5H, m), 7.65,(1H, s), 7.37,(1H, t), 7.03-6.93,(4H, m), 3.83,(3H, s); MS 371 (MH)+; HPLC retention time (system 1) 4.08 minutes.

Workup

  1. customHPLC retention time (system 1) 4.08 minutes

Sources & evidence

ORD record
ord-d3e2abe6ab554d0bb54c25062020a4ae
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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