1H-Indazole → HCID 54413098, compound

HRID 1939990Notes

Reaction equation

HRID 1939990 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[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[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 92211H-IndazoleHCID 11430Potassium CarbonateHCID 109017203-Iodo-4H-chromen-4-one

Product 1

HCID 54413098HCID 54413098, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an eggplant type flask (25 ml), 3-iodochromone (136 mg) prepared in Example 1, indazole (236 mg), potassium carbonate (1382 mg), and dimethylformamide (15 mg) were added and the mixture was reacted at 80° C. for 30 hours with stirring. The reaction mixture was added to ice water and extracted with 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 the purified product was recrystallized from benzene/hexane to give the titled compound (113.6 mg; yield=88.5%) as crystals. Melting point: 237°-238° C. 1H-NMR(CDCl3, δ ppm): 6.94 (s, H3), 8.26 (dd, H5), 7.58-7.68 (m, H6), 7.75 (t, H7), 7.58-7.68 (m, H8), 8.30 (s, H3'), 7.82 (m, H4'), 7.35-7.53 (m, H5'), 7.35-7.53 (m, H6'), 8.26 (m, H7') .

Workup

  1. customthe mixture was reacted at 80° C. for 30 hours
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe purified product was recrystallized from benzene/hexane

Sources & evidence

ORD record
ord-cb22f5da32ab4e8e817ca5cda0b0e551
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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