5-Allyl-2-hydroxy-3-methoxyphenylboronic acid → 6-(2-Hydroxy-5-methoxyphenyl)-6'-(5-allyl-2-hydroxy-3-methoxyphenyl)-2,2'-bipyridine

HRID 566938Notes

Reaction equation

HRID 566938 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:26]1[CH:27]=[C:28]([O:36][CH3:37])[C:29]([OH:35])=[C:30](B(O)O)[CH:31]=1)[CH:24]=[CH2:25]>>[OH:22][C:15]1[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=1[C:10]1[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:30]3[CH:31]=[C:26]([CH2:23][CH:24]=[CH2:25])[CH:27]=[C:28]([O:36][CH3:37])[C:29]=3[OH:35])[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 186169535-Allyl-2-hydroxy-3-methoxyphenylboronic acidHCID 1358542856-Bromo-6'-(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

Product 1

HCID 1355063486-(2-Hydroxy-5-methoxyphenyl)-6'-(5-allyl-2-hydroxy-3-methoxyphenyl)-2,2'-bipyridineYield 42%

Procedure

6-(2-Hydroxy-5-methoxyphenyl)-6′-(5-allyl-2-hydroxy-3-methoxyphenyl)-2,2′-bipyridine was prepared from 6-bromo-6′-(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine and 5-allyl-2-hydroxy-3-methoxyphenylboronic acid in 42% yield using method F; δH [2H6]-DMSO 13.41,(1H, s), 12.52,(1H, s), 8.38,(1H, d), 8.27,(1H, d), 8.24-8.12,(4H, m), 7.65,(1H, s), 7.52,(1H, s), 6.99,(1H, d), 6.93,(2H, m), 6.05,(1H, m), 5.14,(1h, d), 5.07,(1H, d), 3.83,(6H, s), 3.40,(2H, d).

Sources & evidence

ORD record
ord-72df69ca4eb14ab988b3ea9fde7eb89b
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

Loading…