1H-Indazole → HCID 53747324, compound

HRID 1940004Notes

Reaction equation

HRID 1940004 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[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[N:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[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 92211H-IndazoleHCID 11430Potassium CarbonateHCID 8488173-Iodo-7-methoxy-4H-1-benzopyran-4-one

Product 1

HCID 53747324HCID 53747324, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-methoxy-3-iodochromone (151 mg) prepared in Example 21, indazole (236 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 (40.5 mg; yield=27.6%) as golden crystals. Melting point: 218°-220° C. 1H-NMR(CDCl3, δ ppm): 3.97 (s, 3H, CH3O), 6.83 (s, 1H, H3), 8.16 (dd, 1H, H5), 7.02 (s, 1H, H6), 7.01 (s, 1H, H8), 8.27 (s, H3'), 7.36 (d, 1H, H4'), 7.06 (d, 1H, H5'), 7.80 (d, 1H, H6').

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-28bfa457bb134ba38cda816ea3860c02
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

Loading…