Sodium Carbonate → 6,6'-Bis(2-hydroxy-3-ethoxyphenyl)-2,2'-bipyridine

HRID 566914Notes

Reaction equation

HRID 566914 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:15]1(Br)[NH:20][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:18][CH:17]=[CH:16]1.[C:28](=[O:31])([O-])[O-].[Na+].[Na+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:23]1[N:22]=[C:21]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH2:9][CH3:10])[C:28]=3[OH:31])[N:20]=2)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 18617074(3-Ethoxy-2-hydroxyphenyl)boronic acidHCID 186170956,6-Dibromo-2,2'-bipyridyl

Product 1

HCID 1355290156,6'-Bis(2-hydroxy-3-ethoxyphenyl)-2,2'-bipyridineYield 48%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

6,6′-Bis(2-hydroxy-3-ethoxyphenyl)-2,2′-bipyridine was prepared by reaction of 2-hydroxy-3-ethoxyphenylboronic acid (836 mg, 4.60 mmol) with 6,6-dibromo-2,2′-bipyridyl (722 mg, 2.30 mmol), sodium carbonate (2N solution, 6 ml) and tetrakis(triphenylphosphine) palladium (40 mg) in ethylene glycol dimethyl ether (30 ml) at reflux under nitrogen for 4 hours. The solid was filtered from the cooled reaction and washed with ether and water and toluene, to give the desired product as a yellow solid (446 mg, 48%);δH [2H6]-DMSO 8.33,(2H, d), 8.23,(2H, t), 8.14,(2H, d), 7.68,(2H, d), 7.05,(2H, d), 6.88,(2H, t), 4.06,(4H, q), 1.35,(6H, t).

Workup

  1. temperatureat reflux under nitrogen for 4 hours
  2. filtrationThe solid was filtered from the cooled reaction
  3. washwashed with ether and water and toluene

Sources & evidence

ORD record
ord-1fad10c4616a46f59027953650c274f0
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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