Pyrazole → HCID 178487681, compound

HRID 1940002Notes

Reaction equation

HRID 1940002 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:14])[C:8](I)=[CH:9][O:10]2)=[CH:5][CH:4]=1.[NH:15]1[CH:19]=[CH:18][CH:17]=[N:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:15]1[CH:19]=[CH:18][C:17]([C:9]2[O:10][C:11]3[C:6]([C:7](=[O:14])[CH:8]=2)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)=[N:16]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 8488173-Iodo-7-methoxy-4H-1-benzopyran-4-one

Product 1

HCID 178487681HCID 178487681, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-methoxy-3-iodochromone (151 mg) prepared in Example. 21, 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 (90.8 mg; yield=75.0%) as light yellow needle crystals. Melting point: 170°-171° C. 1H-NMR(CDCl3, δ ppm): 3.93 (s, CH3O), 6.56 (hr. s, H3), 8.13 (d, H5), 7.00 (d, H6), 6.94 (d, H8), 6.81 (s, H3'), 7.83 (s, H4'), 8.18 (d, H5').

Workup

  1. extractionextracted from chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customrecrystallized from benzene/hexane

Sources & evidence

ORD record
ord-8d37e19d0fbb4c0d888e3a91398e2052
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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