Sodium Carbonate → 6,6'-Bis(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

HRID 566913Notes

Reaction equation

HRID 566913 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1B(O)O.Br[C:14]1(Br)[NH:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:17][CH:16]=[CH:15]1.[C:27](=[O:30])([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[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:22]1[N:21]=[C:20]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:7]3[CH:6]=[C:5]([O:8][CH3:9])[CH:4]=[CH:3][C:27]=3[OH:30])[N:19]=2)[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 18617021(2-Hydroxy-5-methoxyphenyl)boronic acidHCID 186170956,6-Dibromo-2,2'-bipyridyl

Product 1

HCID 1355369316,6'-Bis(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridineYield 44%

Reagents, catalysts & solvents 2

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

Procedure

6,6′-Bis(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine was prepared by reaction of 2-hydroxy-5-methoxyphenylboronic acid (650 mg, 3.87 mmol) with 6,6-dibromo-2,2′-bipyridyl (520 mg, 1.64 mmol), sodium carbonate (2N solution, 4 ml) and tetrakis(triphenylphosphine) palladium (40 mg) in ethylene glycol dimethyl ether (16 ml) at reflux under nitrogen for 11 hours. The solid was filtered from the cooled reaction and washed with ether and water. The residue was dissolved in toluene and filtered through a short column of silica, washing through with further toluene. The combined filtrate and washings were concentrated under vacuum to give the desired product as a yellow solid (286 mg, 44%); δH [2H6]-DMSO 8.30,(2H, d), 8.13,(4H, m), 7.56,(2H, s), 6.88,(4H, m), 3.73,(6H, s).

Workup

  1. temperatureat reflux under nitrogen for 11 hours
  2. filtrationThe solid was filtered from the cooled reaction
  3. washwashed with ether and water
  4. dissolutionThe residue was dissolved in toluene
  5. filtrationfiltered through a short column of silica
  6. washwashing through with further toluene
  7. concentrationThe combined filtrate and washings were concentrated under vacuum

Sources & evidence

ORD record
ord-229a93abe6964ab686c0d9b5015a1078
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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