2-Hydroxy-3-hexylphenylboronic acid → 6-(2-Hydroxy-3-hexylphenyl)-6'-(2-hydroxy-3-methoxyphenyl)-2,2'-bipyridine

HRID 566929Notes

Reaction equation

HRID 566929 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][CH:17]=[C:16]([O:20][CH3:21])[C:15]=3[OH:22])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[OH:23][C:24]1[C:29]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O>>[OH:23][C:24]1[C:29]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[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]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=3[OH:22])[N:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 186169692-Hydroxy-3-hexylphenylboronic acidHCID 1358542866-Bromo-6'-(2-hydroxy-3-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 1356734326-(2-Hydroxy-3-hexylphenyl)-6'-(2-hydroxy-3-methoxyphenyl)-2,2'-bipyridineYield 68%

Procedure

6-(2-Hydroxy-3-hexylphenyl)-6′-(2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine and 2-hydroxy-3-hexylphenylboronic acid in 68% yield using method F; δH [2H6]-DMSO 13.23,(1H, s), 8.35,(2H, t), 8.27,(2H, m), 8.17,(1H, d), 8.10,(1H, d), 7.97,(1H, d), 7.72,(1H, d), 7.26,(1H, d), 7.09,(1H, d), 6.93,(2H, m), 3.84,(3H, s), 2.68,(2H, t), 1.62,(2H, m), 1.42-1.25(6H, m), 0.88(3H, t); MS 455 (MH)+; HPLC retention time (system 1) 4.94 minutes.

Workup

  1. customHPLC retention time (system 1) 4.94 minutes

Sources & evidence

ORD record
ord-98257a3ee15a47948c0e9eea3cf739e6
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

Loading…