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

HRID 1263580Notes

Reaction equation

HRID 1263580 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.[CH3:22][C:23]1[CH:24]=[CH:25][C:26]([OH:32])=[C:27](B(O)O)[CH:28]=1>>[OH:21][C:15]1[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=1[C:10]1[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:25]3[CH:24]=[C:23]([CH3:22])[CH:28]=[CH:27][C:26]=3[OH:32])[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 18617005(2-Hydroxy-5-methylphenyl)boronic acidHCID 1358542886-Bromo-6'-(2-hydroxy-4-methylphenyl)-2,2'-bipyridine

Product 1

HCID 1356734126-(2-Hydroxy-4-methylphenyl)-6'-(2-hydroxy-5-methylphenyl)-2,2'-bipyridineYield 44%

Procedure

6-(2-Hydroxy-4-methylphenyl)-6′-(2-hydroxy-5-methylphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-4-methylphenyl)-2,2′-bipyridine and 5-methyl-2-hydroxyphenylboronic acid in 44% yield using method F; δH [2H6]-DMSO 13.60,(1H, b), 13.10,(1H, b), 8.32,(2H, t), 8.23,(2H, m), 8.13,(2H, d), 8.03,(1H, d), 7.95,(1H, s), 7.18,(1H, d), 6.92,(1H, d), 6.83,(2H, m), 2.33,(3H, s), 2.34,(3H, s), MS 369 (MH)+; HPLC retention time (system 1) 4.46 minutes.

Workup

  1. customHPLC retention time (system 1) 4.46 minutes

Sources & evidence

ORD record
ord-22207f7008c64bf2a8dd420875a2ef57
Source dataset
uspto-grants-2003_04
Patent number
US06541490B1

Reaction notes

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