Sodium Carbonate → 3-Bromo-5-phenylpyridine

HRID 3331

Reaktionsgleichung

Reaktionsgleichung von HRID 3331
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 693693,5-Dibromopyridine

Produkt 1

HCID 27629043-Bromo-5-phenylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Portions of 3,5-dibromopyridine (1.0 g, 4.22 mmol), phenylboronic acid (570 mg, 4.6 mmol) and palladium tetra(triphenylphosphine) (60 mg) were combined in toluene (20 mL) with aqueous sodium carbonate solution (2M, 3.0 mL) and heated at reflux for 6 hours. The mixture was cooled to ambient temperature, and the solvent was removed. The residue was purified by chromatography (silica gel, eluting with ether:hexane 1:10 to give the title compound: MS (CI/NH3) m/z: 234/236 (M+H)+, 251/153 (M+NH4)+ ; 1H NMR (CDCl3, 300 MHz) δ7.21-8.02 (dd, J=2.0, 2.0 Hz), 8.65 (d, J=2.0 Hz), 8.75 (d, J=2.0 Hz).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. customthe solvent was removed
  4. customThe residue was purified by chromatography (silica gel
  5. washeluting with ether:hexane 1:10

Quellen und Nachweise

ORD-Eintrag
ord-f04c2e1d91b841f084faee8cc1432b9f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733912

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