Pyrazole → HCID 86712410, compound

HRID 628215Notes

Reaction equation

HRID 628215 reaction equation
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

Participants

8

Reactant 4

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

Product 1

HCID 86712410HCID 86712410, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e963c325a1ca47588ca1445589987a02
Source dataset
uspto-grants-2016_04
Patent number
US09312502B2

Reaction notes

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