Pyridine → 4-bromo-1-(2-fluorophenyl)-3-methyl-1H-pyrazole

HRID 601670

Reaction equation

HRID 601670 reaction equation
[Br:1][C:2]1[C:3]([CH3:7])=[N:4][NH:5][CH:6]=1.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1OB(O)O.N1C=CC=CC=1>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[C:3]([CH3:7])=[N:4][N:5]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[F:8])[CH:6]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 222378312-Fluorophenylboric acidHCID 178434489HCID 178434489, compound

Product 1

HCID 231582044-bromo-1-(2-fluorophenyl)-3-methyl-1H-pyrazoleYield 8.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

580 mg of 4-bromo-3-methylpyrazole, 1.0 g of 2-fluorophenylboric acid, 3.3 g of copper acetate, 1.0 g of molecular sieves 4A, and 1.6 ml of pyridine were suspended in 8.0 ml of dimethylformamide, and the mixture was stirred at room temperature for 3 days. The obtained suspended solution was filtrated by celite, and the filtrate was diluted with ethyl acetate. Organic layer was washed with 0.5 N sodium hydride, dried with sodium sulfate, and the solvents were distilled outunder reduced pressure. The residues were purified by silicagel column chromatography (hexane:ethyl acetate=50:50) to obtain 78 mg of the above compound as a crude product.

Workup

  1. filtrationwas filtrated by celite
  2. additionthe filtrate was diluted with ethyl acetate
  3. washOrganic layer was washed with 0.5 N sodium hydride
  4. dry with materialdried with sodium sulfate
  5. distillationthe solvents were distilled outunder reduced pressure
  6. customThe residues were purified by silicagel column chromatography (hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-ce8ea8e801ae44649b68ad6b1075347e
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Linked notes

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