2-Hydroxy-3-hexylphenylboronic acid → HCID 135673430, compound

HRID 566933Notes

Reaction equation

HRID 566933 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.[CH2:23]([C:29]1[C:30]([OH:38])=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[CH2:23]([C:29]1[C:30]([OH:38])=[C:31]([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:32]=[CH:33][CH:34]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 186169692-Hydroxy-3-hexylphenylboronic acidHCID 1358542856-Bromo-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 135673430HCID 135673430, compoundYield 57%

Procedure

6-(3-Hexyl-2-hydroxyphenyl)-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine and 3-hexyl-2-hydroxyphenylboronic acid in 57% yield using method F; δH [2H6]-DMSO 12.40,(1H, s), 8.36,(2H, m), 8.25,(2H, t), 8.18,(1H, d), 8.09,(1H, d), 7.96,(1H, d), 7.65,(1H, s), 7.25,(1H, d), 6.99,(1H, d), 6.96-6.8,(2H, m), 3.81,(3H, s), 2.67,(2H, t), 1.60,(2H, m), 1.42-1.25,(6H, m), 0.88,(3H, t); MS 455 (MH)+; HPLC retention time (system 1) 4.96 minutes.

Workup

  1. customHPLC retention time (system 1) 4.96 minutes

Sources & evidence

ORD record
ord-e464c47330d94237920a2ade46021fb3
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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