Pyrazole → HCID 28923713, compound

HRID 720263Notes

Reaction equation

HRID 720263 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@@H:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[NH:11]1[CH:15]=[CH:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.[Cu]I>[N:11]1([C:2]2[CH:3]=[C:4]([C@@H:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=[N:12]1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 9952938(S)-1-(3-bromophenyl)ethanamine

Product 1

HCID 28923713HCID 28923713, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
195 °C

Procedure

To a solution of (S)-1-(3-bromo-phenyl)-ethylamine (1.5 g, 7.5 mmol) and pyrazole (1.02 g, 15 mmol) in N-methylpyrrolidinone (10 mL) in a quartz tube were added potassium carbonate (2.1 g, 15 mmol), and copper (1) iodide (143 mg, 0.75 mmole), and the resulting mixture was heated at 195° C. for 5 h in a Mars 5 microwave oven (600 W). The reaction mixture was cooled down to room temperature and filtered. The crude product was purified by flash chromatography (10% MeOH/89% EtOAc/1% triethylamine) to provide the title compound (814 mg, 58% yield) as a brown oil.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationfiltered
  3. customThe crude product was purified by flash chromatography (10% MeOH/89% EtOAc/1% triethylamine)

Sources & evidence

ORD record
ord-a2c5bdad4f314c1c9d0dead32160e32b
Source dataset
uspto-grants-2006_11
Patent number
US07135472B2

Reaction notes

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