Carbazole → HCID 59399028, Verbindung

HRID 1038297

Reaktionsgleichung

Reaktionsgleichung von HRID 1038297
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH:25]1[C:37]2[NH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]=2[CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>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].O.CCCCCC.C1(C)C(C)=CC=CC=1>[C:19]1([C:10]2[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:8]([C:5]3[CH:6]=[CH:7][C:2]([N:36]4[C:37]5[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=5[C:30]5[C:35]4=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:3][CH:4]=3)[N:9]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

9

Edukt 4

HCID 6854CarbazoleHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 46450961-(p-Bromophenyl)-3,5-diphenylpyrazoleHCID 23676156Sodium t-butoxide

Produkt 1

HCID 59399028HCID 59399028, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 962WaterLösungsmittelHCID 7237O-XyleneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

In a 100 mL three-necked flask were placed 1.5 g (4.0 mmol) of 1(4-bromophenyl)-3,5-diphenyl-1H-pyrazol, 0.70 g (4.2 mmol) of 9H-carbazole, and 0.80 g (8.2 mmol) of sodium tert-butoxide, and the atmosphere in the flask was replaced with nitrogen. To this mixture was added 40 mL of xylene. The mixture was degassed by being stirred under reduced pressure, and then to this mixture were added 0.10 mL of a 10% hexane solution of tri(tert-butyl)phosphine and 50 mg (0.086 mmol) of bis(dibenzylideneacetone)palladium(0). The resulting mixture was stirred under a nitrogen stream at 140° C. for 6 hours. After a certain time, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined, washed with water, a saturated aqueous solution of sodium hydrogen carbonate, and saturated saline, and dried with magnesium sulfate. The filtrate obtained by gravity filtering the obtained mixture was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (a developing solvent was a mixed solvent of toluene:hexane=1:1) to give an oily substance. To the oily substance was added hexane, and suction filtration was performed on a precipitated solid, so that 1.3 g of a white powder, which was the object of the synthesis, was obtained at a yield of 68%.

Aufarbeitung

  1. customIn a 100 mL three-necked flask were placed
  2. customThe mixture was degassed
  3. stirringThe resulting mixture was stirred under a nitrogen stream at 140° C. for 6 hours
  4. extractionan aqueous layer was extracted with toluene
  5. extractionThe obtained extracted solution
  6. washwashed with water
  7. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and saturated saline, and dried with magnesium sulfate
  8. customThe filtrate obtained by gravity
  9. filtrationfiltering the obtained mixture
  10. concentrationwas concentrated
  11. customto give an oily substance
  12. customThe obtained oily substance was purified by silica gel column chromatography (a developing solvent
  13. customhexane=1:1) to give an oily substance
  14. additionTo the oily substance was added
  15. filtrationhexane, and suction filtration
  16. customthe object of the synthesis
  17. customwas obtained at a yield of 68%

Quellen und Nachweise

ORD-Eintrag
ord-39071021d06549a483a6e8e2d5a31263
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551625B2

Verknüpfte Notizen

Wird geladen…