3-Methoxy-2-Hydroxyphenyl Boronic Acid → 6-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

HRID 1263575Notes

Reaction equation

HRID 1263575 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]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O>>[OH:22][C:23]1[C:28]([O:29][CH3:30])=[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 186169703-Methoxy-2-Hydroxyphenyl Boronic AcidHCID 1358542886-Bromo-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

Product 1

HCID 1356734186-(2-Hydroxy-3-methoxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridineYield 33%

Procedure

6-(2-Hydroxy-3-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-3-methoxyphenylboronic acid in 33% yield using method F; δH [2H6]-DMSO 13.52,(2H, b), 8.31,(2H, dd), 8.26,(1H, d), 8.21,(1H, d), 8.12,(1H, d), 8.02,(1H, d), 7.70,(1H, d), 7.09,(1H, d), 6.92,(1H, t), 6.82,(1H, d), 3.86,(3H, s), 2.32,(3H, s); MS 385 (MH)+; HPLC retention time (system 1) 4.21 minutes.

Workup

  1. customHPLC retention time (system 1) 4.21 minutes

Sources & evidence

ORD record
ord-496a113a29cb47f19c6743beae2ed597
Source dataset
uspto-grants-2003_04
Patent number
US06541490B1

Reaction notes

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