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

HRID 1263568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1263568
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4fc79a2ea86448c490b18ecbb0e0abfd
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541490B1

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