Pyridine → methyl 4-nitro-1-phenyl-1H-pyrazole-3-carboxylate

HRID 733117Notes

Reaction equation

HRID 733117 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([O-:11])=[O:10])=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[C:12]1(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=C[CH:23]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N+:1]([C:4]1[C:5]([C:9]([O:11][CH3:23])=[O:10])=[N:6][N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 78412Phenyl dihydrogen orthoborateHCID 178524955HCID 178524955, compound

Product 1

HCID 23084897methyl 4-nitro-1-phenyl-1H-pyrazole-3-carboxylateYield 83.8%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-nitro-1H-pyrazole-3-carboxylate (1.0 g, 5.84 mmol) in methylene chloride (20 mL) were added phenylboric acid (1.43 g, 11.7 mmol), copper(II) acetate (1.60 g, 8.76 mmol) and pyridine (2 mL, 23.4 mmol), and the mixture was stirred overnight at room temperature under an air atmosphere. After removal of the insolubles by filtration, the filtrate was washed with water (twice) and saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the title compound (1.21 g, 83.5%).

Workup

  1. customAfter removal of the insolubles
  2. filtrationby filtration
  3. washthe filtrate was washed with water (twice) and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86bc90e3542c49b6800c68c6eec4cc6f
Source dataset
uspto-grants-2009_09
Patent number
US07589096B2

Reaction notes

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