Sodium Carbonate → Bis(2-hydroxy-3,5-dimethylphenyl)-2,2'-bipyridine

HRID 566915Notes

Reaction equation

HRID 566915 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([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[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[C:16]1[CH:15]=[CH:14][N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[C:17]=1[C:7]1[CH:6]=[C:5]([CH3:9])[CH:4]=[C:3]([CH3:2])[C:27]=1[OH:30]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 18617001(2-Hydroxy-3,5-dimethylphenyl)boronic acidHCID 186170956,6-Dibromo-2,2'-bipyridyl

Product 1

HCID 136082253Bis(2-hydroxy-3,5-dimethylphenyl)-2,2'-bipyridineYield 68%

Reagents, catalysts & solvents 2

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

Procedure

Bis(2-hydroxy-3,5-dimethylphenyl)-2,2′-bipyridine was prepared by reaction of 2-hydroxy-3,5-dimethylphenylboronic acid (321 mg, 1.92 mmol) with 6,6-dibromo-2,2′-bipyridyl (260 mg, 0.82 mmol), sodium carbonate (2N solution, 2 ml) and tetrakis(triphenylphosphine) palladium (20 mg) in ethylene glycol dimethyl ether (8 ml) at reflux under nitrogen for 88 hours. The solid was filtered from the cooled reaction and washed with acetone and water to give the desired product as a yellow solid (220 mg, 68%); δH [21H6]-DMSO 8.39,(2H, d), 8.31,(2H, t), 8.10,(2H, 7.78,(2H, s), 7.10,(2H, s), 2.31,(6H, s), 2.24,(6H, s).

Workup

  1. temperatureat reflux under nitrogen for 88 hours
  2. filtrationThe solid was filtered from the cooled reaction
  3. washwashed with acetone and water

Sources & evidence

ORD record
ord-bd1ab7200f7f4a76ab8efbffe32e34b1
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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