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

HRID 341056

Reaction equation

HRID 341056 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=O)[C:12]([C:21](OCC)=[O:22])=[CH:11]1.P(Cl)(Cl)(Cl)=O.[F:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[NH:38][NH2:39].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2=[N:39][N:38]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[F:31])[C:21](=[O:22])[C:12]2=[CH:11]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 4238442-Fluorophenylhydrazine hydrochlorideHCID 68153945Ethyl 1-[(2-fluoro-4-iodophenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 671125025-[(2-fluoro-4-iodophenyl)methyl]-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazol[4,3-c]quinolin-3-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

Ethyl 1-[(2-fluoro-4-iodophenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate (1.4 g, 3.1 mmol) was dissovled in phosphorus oxychloride (6.0 mL, 64 mmol, 21 equiv) and stirred for 2.5 hours at ambient temperature. The mixture was diluted with toluene (10 mL) and concentrated in vacuo. The residue was dissolved in dioxane (17 mL), treated with 2-fluorophenylhydrazine (0.87 g, 6.8 mmol, 2.2 equiv) and potassium carbonate (1.3 g, 9.4 mmol, 3 equiv) and stirred at ambient temperature for 5 minutes. The mixture was placed into a preheated oil bath at 80° C. for 1 hour, cooled to ambient temperature and diluted with chloroform (150 mL). The organic mixture was washed once with water (50 mL) and brine (50 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with a chloroform:methanol (95:5) solution (30 mL). The solid was filtered and dried in vacuo, providing the titled compound.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dioxane (17 mL)
  3. stirringstirred at ambient temperature for 5 minutes
  4. waitThe mixture was placed into a preheated oil bath at 80° C. for 1 hour
  5. temperaturecooled to ambient temperature
  6. washThe organic mixture was washed once with water (50 mL) and brine (50 mL)
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with a chloroform:methanol (95:5) solution (30 mL)
  11. filtrationThe solid was filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-e08fecfcf6ce423885e283eb09c67de2
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Linked notes

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