3-Fluoro-2-hydroxybenzeneboronic acid → 6-(3-Fluoro-2-hydroxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

HRID 566923Notes

Reaction equation

HRID 566923 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.[F:22][C:23]1[C:24]([OH:32])=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1>>[F:22][C:23]1[C:24]([OH:32])=[C:25]([C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=4[OH:21])[N:9]=3)[CH:5]=[CH:4][CH:3]=2)[CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 186170523-Fluoro-2-hydroxybenzeneboronic acidHCID 1358542886-Bromo-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

Product 1

HCID 1355441546-(3-Fluoro-2-hydroxyphenyl)-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridineYield 17%

Procedure

6-(3-Fluoro-2-hydroxyphenyl)-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine and 3-fluoro-2-hydroxyphenylboronic acid in 17% yield using method F; δH [2H6]-DMSO 13.37,(1H, b), 8.38,(1H, d), 8.34-8.15,(4H, m), 8.10,(1H, d), 8.01,(1H, d), 7.95,(1H, d), 7.34,(1H, t), 6.98,(1H, m), 6.81,(2H, m), 2.33,(3H, s).

Sources & evidence

ORD record
ord-2bdb0bb8af1a4119ae874cd1d353780d
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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