(2-Hydroxyphenyl)boronic acid → 6-(2-Hydroxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

HRID 566919Notes

Reaction equation

HRID 566919 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][C:17]([CH3:20])=[CH:16][C:15]=3[OH:21])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[OH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O>>[OH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=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][C:17]([CH3:20])=[CH:16][C:15]=3[OH:21])[N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2773454(2-Hydroxyphenyl)boronic acidHCID 1358542886-Bromo-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

Product 1

HCID 1356734166-(2-Hydroxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridineYield 68%

Procedure

6-(2-Hydroxyphenyl)-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine and 2-hydroxyphenylboronic acid in 68% yield using method F; δH [2H6]-DMSO 13.55,(1H, b), 13.39,(1H, b), 8.38-8.32,(4H, m), 8.30-8.20,(4H, m), 8.13,(3H, d), 8.03,(1H, d), 7.37,(1H, t), 7.00,(2H, m), 6.81,(2H, m), 2.30,(3H, s); MS 355 (MH)+; HPLC retention time (system 1) 4.34 minutes.

Workup

  1. customHPLC retention time (system 1) 4.34 minutes

Sources & evidence

ORD record
ord-37dfd2a269ce4ba9a331f23f6907ad05
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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