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

HRID 566916Notes

Reaction equation

HRID 566916 reaction equation
[F:1][C:2]1[C:3]([OH:11])=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:13]1(Br)[NH:18][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:16][CH:15]=[CH:14]1.[C:26](=[O:29])([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:11][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:21]1[N:20]=[C:19]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:26]=3[OH:29])[N:18]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 186170523-Fluoro-2-hydroxybenzeneboronic acidHCID 186170956,6-Dibromo-2,2'-bipyridyl

Product 1

HCID 1354560156,6'-Bis(2-hydroxy-3-fluorophenyl)-2,2'-bipyridineYield 39%

Reagents, catalysts & solvents 2

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

Procedure

6,6′-Bis(2-hydroxy-3-fluorophenyl)-2,2′-bipyridine was prepared by reaction of 3-fluoro-2-hydroxyphenylboronic acid (600 mg, 3.84 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 7 hours. The solid was filtered from the cooled reaction and washed with ethylene glycol dimethyl ether and water to give the desired product as a beige solid (240 mg, 39%); δH [2H6]-DMSO 8.49,(2H, d), 8.30,(4H, m), 8.00,(2H, d), 7.37,(2H, t), 6.99,(2H, dd).

Workup

  1. temperatureat reflux under nitrogen for 7 hours
  2. filtrationThe solid was filtered from the cooled reaction
  3. washwashed with ethylene glycol dimethyl ether and water

Sources & evidence

ORD record
ord-3f8253bf39044be1803a2bdeae276000
Source dataset
uspto-grants-2001_01
Patent number
US06177419B1

Reaction notes

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