Potassium Carbonate → 2-(2-fluorophenyl)-5-[(4-iodophenyl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

HRID 449953Notes

Reaction equation

HRID 449953 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][N:10]=[C:11]2[C:15](=[O:16])[N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[N:13]=[C:12]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2F)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CS(C)=O>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:14]1[C:15](=[O:16])[C:11]2=[N:10][N:9]([CH2:8][C:5]3[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[C:12]2=[N:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 178516808HCID 178516808, compound

Product 1

HCID 468965122-(2-fluorophenyl)-5-[(4-iodophenyl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,3-Bis(2-fluorophenyl)-1H-pyrazole-4,5-dione 4-{[(4-iodophenyl)methyl]hydrazone} (50 mg, 0.097 mmol) was dissolved in degassed dimethylsulfoxide (3.5 mL), treated with potassium carbonate (120 mg, 0.87 mmol, 9.0 equiv) and placed into an oil bath preheated to 120° C. for 15 minutes. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (50 mL, aqueous saturated) and extracted with ethyl acetate (2×75 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 20:80; hexanes:ethyl acetate), providing the titled compound as a dark red solid: 1H-NMR (400 MHz, CDCl3) δ 8.32 (1H, d, J=7.7 Hz), 7.70 (2H, d, J=8.3 Hz), 7.66-7.62 (1H, m), 7.59-7.55 (2H, m), 7.49 (1H, d, J=8.9 Hz), 7.42-7.36 (1H, m), 7.31-7.25 (2H, m), 7.07 (2H, d, J=8.0 Hz), 5.77 (2H, s) ppm; high resolution mass spectrometry (ES+) m/z 497.0278 [(M+H)+; calculated for C22H15FIN4O: 497.0269].

Workup

  1. customplaced into an oil bath
  2. extractionextracted with ethyl acetate (2×75 mL)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel gradient chromatography (100:0 to 20:80; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-54443c0354364b02b47790fd775b3be5
Source dataset
uspto-grants-2013_07
Patent number
US08486946B2

Reaction notes

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