(2-Hydroxy-3-methylphenyl)boronic acid → 6-(2-Hydroxy-3-methylphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

HRID 1263577Notes

Reaction equation

HRID 1263577 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[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O>>[OH:22][C:23]1[C:28]([CH3:29])=[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 18616946(2-Hydroxy-3-methylphenyl)boronic acidHCID 1358542886-Bromo-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

Product 1

HCID 1354877046-(2-Hydroxy-3-methylphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridineYield 84%

Procedure

6-(2-Hydroxy-3-methylphenyl)-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine and 2-hydroxy-3-methylphenylboronic acid in 84% yield using method F; δH [2H6]-DMSO 13.38,(1H, b), 8.41-8.22,(4H, m), 8.13,(1H, d), 8.09-8.01,(2H, m), 7.96,(1H, d), 7.28,(1H, d), 6.90,(1H, t), 6.80,(2H, m), 2.33,(3H, s), 2.26,(3H, s); MS 369 (MH)+; HPLC retention time (system 1) 4.53 minutes.

Workup

  1. customHPLC retention time (system 1) 4.53 minutes

Sources & evidence

ORD record
ord-87d9b727bd0a4d02a433821092e1bfc5
Source dataset
uspto-grants-2003_04
Patent number
US06541490B1

Reaction notes

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