Pyrazole → HCID 178493396, compound

HRID 1940000Notes

Reaction equation

HRID 1940000 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:16])[C:6](I)=[CH:7][O:8]2.[NH:17]1[CH:21]=[CH:20][CH:19]=[N:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:17]1[CH:21]=[CH:20][C:19]([C:7]2[O:8][C:9]3[C:4]([C:5](=[O:16])[CH:6]=2)=[C:3]([O:2][CH3:1])[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=3)=[N:18]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 21465560HCID 21465560, compound

Product 1

HCID 178493396HCID 178493396, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5,7-dimethoxy-3-iodochromone (166 mg) prepared in Example 16, 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 purified by the silica gel column chromatography, and recrystallized from benzene/hexane to give the titled compound (122 mg; yield=90.0%) as white bulk crystals. Melting point: 197°-198° C. Mass spectrum (M+): 272. 1 H-NMR(CDCl3, δ ppm): 6.77 (s, 1H, H3), 6.55 (d, 1H, H6), 7.81 (s, 1H, H8), 8.12 (s, 1H, H3'), 6.41 (d, H4'), 6.54 (s, 1H, H5'), 3.96 (s, 3H, 5MeO), 4.06 (s, 3H, 7MeO).

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. customThe residue was purified by the silica gel column chromatography
  6. customrecrystallized from benzene/hexane

Sources & evidence

ORD record
ord-f8b4928d9c93490fb4e63f39b94eeb94
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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