Pyrazole → HCID 178515694, compound

HRID 1940006Notes

Reaction equation

HRID 1940006 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]=[C:6](I)[C:5]2=[O:13].[NH:14]1[CH:18]=[CH:17][CH:16]=[N:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:14]1[CH:18]=[CH:17][C:16]([C:7]2[O:8][C:9]3[C:4]([C:5](=[O:13])[CH:6]=2)=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=3)=[N:15]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 116666776-Chloro-3-iodochromone

Product 1

HCID 178515694HCID 178515694, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-3-iodochromone (153 mg) prepared in Example 28, pyrazole (136 mg), potassium carbonate (1382 mg), and dimethylformamide (15 ml) was reacted at 80° C. for 2 hours with stirring. The reaction mixture was added to ice water and extracted from chloroform. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purifiedby the silica gel column chromatography, and recrystallized from benzene/hexane to give the titled compound (41.9 mg; yield=34.0%) as orange crystals. Melting point: 217°-219° C. Mass spectrum (M+): 246.5.

Workup

  1. customwas reacted at 80° C. for 2 hours
  2. extractionextracted from chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customrecrystallized from benzene/hexane

Sources & evidence

ORD record
ord-07a0ec2f76324f58a88e4a72205ab412
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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