Potassium Phosphate, Tribasic → 2,5-diphenylpyridine

HRID 1897973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1897973
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[C:9]1([C:2]2[CH:7]=[CH:6][C:5]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 693532,5-Dibromopyridine

Produkt 1

HCID 27628582,5-diphenylpyridineAusbeute 91,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2,5-dibromopyridine (10 g, 42 mmol), phenylboronic acid (13.4 g, 110 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (S-Phos) (0.7 g, 1.6 mmol), and potassium phosphate (22 g, 105 mmol) were mixed in 200 mL of toluene and 20 mL of water. Nitrogen is bubbled directly into the mixture for 30 minutes. Next, Pd2(dba)3 was added (0.38 g, 0.4 mmol) and the mixture was heated to reflux under nitrogen for 2 h. The mixture was cooled and the organic layer was separated. The organic layers are washed with brine, dried over magnesium sulfate, filtered, and evaporated to a residue. The residue was purified by column chromatography eluting with 10% ethyl acetate/hexanes. 7 g of desired product was obtained after purification. (91.8% yield)

Aufarbeitung

  1. customNitrogen is bubbled directly into the mixture for 30 minutes
  2. additionNext, Pd2(dba)3 was added (0.38 g, 0.4 mmol)
  3. temperaturethe mixture was heated
  4. temperatureto reflux under nitrogen for 2 h
  5. temperatureThe mixture was cooled
  6. customthe organic layer was separated
  7. washThe organic layers are washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated to a residue
  11. customThe residue was purified by column chromatography
  12. washeluting with 10% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-40e2769d76e74b13b3339a09d724b6f7
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08519384B2

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