Indole → HCID 21465588, compound

HRID 1939991Notes

Reaction equation

HRID 1939991 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]=[CH: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)[CH:15]=[C:14]1[C:3]1[O:4][C:5]2[C:10]([C:11](=[O:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 798IndoleHCID 11430Potassium CarbonateHCID 109017203-Iodo-4H-chromen-4-one

Product 1

HCID 21465588HCID 21465588, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an eggplant type flask (25 ml), 3-iodochromone (136 prepared in Example 1, indole (234 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 ghromatography, and the purified product was recrystallized from benzene/hexane to give the titled compound (42.3 mg; yield=32.2%) as crystals. Melting point: 157°-158° C. 1H-NMR(CDCl3, δ ppm): 6.46 (s, H3), 8.26 (dd, H5), 7.47 (t, H6), 7.72 (t, H7), 7.58 (d, H8), 7.55 (d, H2'), 6.80 (d, H3'), 7.66 (d, H4'), 7.28-7.42 (m, H5'), 7.28-7.42 (m, H6'), 7.99 (m, H7').

Workup

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

Sources & evidence

ORD record
ord-0fcb898efae74eea84ec58f93e7027bb
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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