Pyrazole → HCID 86712410, Verbindung

HRID 628215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628215
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[CH:3]=1.[NH:21]1[CH:25]=[CH:24][CH:23]=[N:22]1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>ClCCl.[Cu]I.CS(C)=O>[C:4]1([N:5]2[C:6]3[CH:11]=[C:10]([N:21]4[CH:25]=[CH:24][CH:23]=[N:22]4)[CH:9]=[CH:8][C:7]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:12]=[CH:13][CH:14]=[CH:2][CH:3]=1

Komponenten

8

Edukt 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 668380442-Bromo-9-phenyl-9H-carbazole

Produkt 1

HCID 86712410HCID 86712410, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A pressure vessel was charged with 2-bromo-9-phenyl-9H-carbazole (10 mmol), pyrazole (20 mmol), potassium carbonate (20 mmol), L-proline (2 mmol), copper(I) iodide (1 mmol), and dimethyl sulfoxide (25 mL). After three cycles of evacuation and backfilling with nitrogen, the vessel was sealed and stirred at 90° C. for three days. After cooling, the reaction mixture was diluted with dichloromethane (200 mL), washed four times with water (200 mL), and dried over magnesium sulfate. After removing the solvent under reduced pressure, the crude product was chromatographed over silica with hexane as the eluent, giving 9-phenyl-2-(1H-pyrazol-1-yl)-9H-carbazole in 45% yield.

Aufarbeitung

  1. customAfter three cycles of evacuation and backfilling with nitrogen, the vessel was sealed
  2. temperatureAfter cooling
  3. washwashed four times with water (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. customAfter removing the solvent under reduced pressure
  6. customthe crude product was chromatographed over silica with hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-e963c325a1ca47588ca1445589987a02
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09312502B2

Notizen zur Reaktion

Wird geladen…