(2-Hydroxy-5-methoxyphenyl)boronic acid → 6-(2-Hydroxy-5-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

HRID 1263576Notes

Reaction equation

HRID 1263576 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][C:26]([O:29][CH3:30])=[CH:25][C:24]=1B(O)O>>[OH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[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 18617021(2-Hydroxy-5-methoxyphenyl)boronic acidHCID 1358542886-Bromo-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

Product 1

HCID 1354309196-(2-Hydroxy-5-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridineYield 28%

Procedure

6-(2-Hydroxy-5-methoxyphenyl)-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine and 2-hydroxy-5-methoxyphenylboronic acid in 28% yield using method F; δH [2H6]-DMSO 13.70,(1H, b), 12.57,(1H, b), 8.38,(1H, d), 8.31,(1H, d), 8.25-8.17,(2H, m), 8.12,(1H, d), 8.02,(1H, d), 7.65,(1H, d), 7.00,(1H, dd), 6.94,(1H, d), 6.82,(2H, m), 3.82,(3H, s), 2.33,(3H, s); MS 385 (MH)+; HPLC retention time (system 1) 4.28 minutes.

Workup

  1. customHPLC retention time (system 1) 4.28 minutes

Sources & evidence

ORD record
ord-21ed9065bd64425b9c7c3be19c6fd761
Source dataset
uspto-grants-2003_04
Patent number
US06541490B1

Reaction notes

Loading…