Pyrazole → HCID 178515693, compound

HRID 1939986Notes

Reaction equation

HRID 1939986 reaction equation
I[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][CH:3]=1.[NH:13]1[CH:17]=[CH:16][CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:13]1[CH:17]=[CH:16][C:15]([C:3]2[O:4][C:5]3[C:10]([C:11](=[O:12])[CH:2]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[N:14]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 109017203-Iodo-4H-chromen-4-one

Product 1

HCID 178515693HCID 178515693, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an eggplant type flask (20 ml), 3-iodochromone (136 mg) prepared in Example 1, pyrazole (136 mg), potassium carbonate (1382 mg), and dimethylformamide (15 ml) were added and the mixture was reacted at 80° C. for 20 hours with stirring. The reaction mixture was added to ice water and extracted with chloroform. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purifiedby the silica gel column chromatography, and the purified compound was recrystallized from benzene/hexane to give the titled compound (75.1 mg; yield=70.8%) as white needle crystals. Melting point: 143°-144° C. 1 H-NMR(CDCl3, δ ppm): 6.90 (s, H3), 8.24 (dd, H5), 7.46-7.58 (m, H6), 7.76 (t, H7), 7.46-7.58 (m ,H8), 7.85 (d, H3'), 6.59 (dd, H4'), 8.23 (d, H5').

Workup

  1. customthe mixture was reacted at 80° C. for 20 hours
  2. extractionextracted with chloroform
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe purified compound was recrystallized from benzene/hexane

Sources & evidence

ORD record
ord-cd0f794ffc0d463bb0fa173ed03695b0
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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