Pyridine → HCID 86257708, compound

HRID 1754381Notes

Reaction equation

HRID 1754381 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[N+:11]([C:14]1[CH:15]=[N:16][NH:17][CH:18]=1)([O-:13])=[O:12].N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:16]2[CH:15]=[C:14]([N+:11]([O-:13])=[O:12])[CH:18]=[N:17]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 163764-nitro-1H-pyrazoleHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 86257708HCID 86257708, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluorobenzeneboronic acid (2.47 g, 17.7 mmol), 4-nitro-1H-pyrazole (1.00 g, 8.84 mmol), copper (II) acetate (2.41 g, 13.3 mmol) and pyridine (2.86 mL, 35.4 mmol) in CH2Cl2 (40 mL) was stirred at room temperature overnight. The reaction mixture was filtered and diluted with water (40 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (SiO2, 0-20% EtOAc/hexanes gradient elution) to give 1-(4-fluorophenyl)-4-nitropyrazole as a white solid (0.820 g, 22%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with water (40 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (SiO2, 0-20% EtOAc/hexanes gradient elution)

Sources & evidence

ORD record
ord-e4b8a40c97e249c39c296169a805835f
Source dataset
uspto-grants-2015_10
Patent number
US09169248B2

Reaction notes

Loading…