Toluene → 2-([1,1'-Biphenyl]-3-yl)-4,5-dimethylpyridine

HRID 2400236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2400236
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[C:11]([CH3:13])[C:10](Br)=[CH:9][N:8]=2)[CH:2]=1.[CH3:21]B1OB(C)OB(C)O1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=C(C3C(OC)=CC=CC=3OC)C=CC=2)CCCCC1.O>[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[C:11]([CH3:13])[C:10]([CH3:21])=[CH:9][N:8]=2)[CH:2]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 574072TrimethylboroxineHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 710081052-([1,1'-Biphenyl]-3-yl)-5-bromo-4-methylpyridine

Produkt 1

HCID 592948462-([1,1'-Biphenyl]-3-yl)-4,5-dimethylpyridineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 58401078Dicyclohexyl(2',6'-dimethoxybiphenyl-3-yl)phosphineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

2-([1,1′-Biphenyl]-3-yl)-5-bromo-4-methylpyridine 11.5 g (35.5 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (5.57 g, 44.3 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (1.2 g, 2.84 mmol), Pd2dba3 (0.650 g, 0.709 mmol) and potassium phosphate tribasic monohydrate, 250 mL toluene and 25 mL of water were placed in flask under nitrogen. The reaction mixture was degassed with nitrogen for 20 minutes and heated to reflux for 24 h. After cooling, the organic layer was separated and the aqueous layer extracted 3×50 mL with dichloromethane, dried over sodium sulfate and evaporated. The crude product was chromatographed on silica gel with 5% dichloromethane in hexane to give 8.0 g (87%) of the product. The product was confirmed by NMR and GC/MS.

Aufarbeitung

  1. customThe reaction mixture was degassed with nitrogen for 20 minutes
  2. temperatureheated
  3. temperatureto reflux for 24 h
  4. temperatureAfter cooling
  5. customthe organic layer was separated
  6. extractionthe aqueous layer extracted 3×50 mL with dichloromethane
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe crude product was chromatographed on silica gel with 5% dichloromethane in hexane

Quellen und Nachweise

ORD-Eintrag
ord-159c40f7b7d946e198d822c08393aa61
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08795850B2

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