5-Fluoro-2-hydroxyphenylboronic acid → 6-(5-Fluoro-2-hydroxyphenyl)-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

HRID 1263590Notes

Reaction equation

HRID 1263590 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]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=3[OH:22])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[F:23][C:24]1[CH:25]=[CH:26][C:27]([OH:33])=[C:28](B(O)O)[CH:29]=1>>[F:23][C:24]1[CH:29]=[CH:28][C:27]([OH:33])=[C:26]([C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=4[OH:22])[N:9]=3)[CH:5]=[CH:4][CH:3]=2)[CH:25]=1

Participants

3

Reactant 2

HCID 37724765-Fluoro-2-hydroxyphenylboronic acidHCID 1358542856-Bromo-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 1355289656-(5-Fluoro-2-hydroxyphenyl)-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridineYield 50%

Procedure

6-(5-Fluoro-2-hydroxyphenyl)-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine and 5-fluoro-2-hydroxyphenylboronic acid in 50% yield using method F; δH [2H6]-DMSO 13.09,(1H, b), 12.63,(1H, b), 8.36,(2H, m), 8.22,(4H, m), 7.99,(1H, d), 7.64,(1H, s), 7.22,(1H, t), 7.05-6.91,(3H, m), 3.80,(3H, s).

Sources & evidence

ORD record
ord-e6e1acc704bb47139195ba771882b75b
Source dataset
uspto-grants-2003_04
Patent number
US06541490B1

Reaction notes

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