Toluene → 3-{10-[4-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9-anthryl}pyridine

HRID 446656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446656
Br[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:22]1([C:28]2[O:32][C:31]([C:33]3[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=3)=[N:30][N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[C:22]1([C:28]2[O:32][C:31]([C:33]3[CH:38]=[CH:37][C:36]([C:2]4[C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[C:9]([C:16]5[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=5)=[C:8]5[C:3]=4[CH:4]=[CH:5][CH:6]=[CH:7]5)=[CH:35][CH:34]=3)=[N:30][N:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 579673303-(10-Bromoanthracen-9-yl)pyridineHCID 583436864-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenylboronic acid

Produkt 1

HCID 595014033-{10-[4-(5-Phenyl-1,3,4-oxadiazol-2-yl)phenyl]-9-anthryl}pyridineAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a 100 mL three-necked flask were placed 0.66 g (2.0 mmol) of 3-(10-bromo-9-anthryl)pyridine, 0.63 g (2.4 mmol) of 4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenylboronic acid, 0.45 g (4.0 mmol) of sodium carbonate, 25 mL of toluene, 3 mL of water, and 6 mL of ethanol. The mixture was degassed by being stirred under reduced pressure, and the atmosphere in the flask was replaced with nitrogen. To this mixture was added 58 mg (0.050 mmol) of tetrakis(triphenylphosphine)palladium(0), and the resulting mixture was refluxed under a nitrogen stream at 120° C. for 23 hours. After a predetermined time has passed, water was added to this mixture, and the aqueous layer was extracted with ethyl acetate. The obtained extract and the organic layer were combined and washed with saturated brine, and then the organic layer was dried with magnesium sulfate. The obtained mixture was subjected to gravity filtration, and the resulting filtrate was concentrated to give a solid. The obtained solid was purified by silica gel column chromatography (a 5:1 ratio of toluene to ethyl acetate). Recrystallization from a mixed solvent of toluene and hexane gave 0.65 g of a solid in 69% yield, which was the desired substance.

Aufarbeitung

  1. customIn a 100 mL three-necked flask were placed
  2. customThe mixture was degassed
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. extractionThe obtained extract
  5. washwashed with saturated brine
  6. dry with materialthe organic layer was dried with magnesium sulfate
  7. filtrationThe obtained mixture was subjected to gravity filtration
  8. concentrationthe resulting filtrate was concentrated
  9. customto give a solid
  10. customThe obtained solid was purified by silica gel column chromatography (a 5:1 ratio of toluene to ethyl acetate)
  11. customRecrystallization from a mixed solvent of toluene and hexane

Quellen und Nachweise

ORD-Eintrag
ord-a1aa4804dd394a5da7747cd11211d3f6
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481176B2

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