Indole → HCID 21465573, compound

HRID 1939997Notes

Reaction equation

HRID 1939997 reaction equation
Br[C:2]1[C:11](=[S: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](=[S:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 798IndoleHCID 11430Potassium CarbonateHCID 57281258HCID 57281258, compound

Product 1

HCID 21465573HCID 21465573, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an eggplant type flask (25 ml), 3-bromothiochromone (121 mg) prepared in Example 8, indole (234 mg), potassium carbonate (1382 mg), and dimethylformamide (15 ml) were added. The mixture was reacted at 80° C. for 20 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 colunm chromatography and recrystallized from benzene/hexane to give the titled compound (118.5 mg; yield=40.4%) as crystals. Melting point: 155°-156° C. 1H-NMR(CDCl3, δ ppm): 7.22 (s, H3), 8.57 (d, H5), 7.55-7.72 (m, H6), 7.55-7.72 (m, H7), 7.55-7.72 (m, H8), 7.45 (d, H2'), 6.79 (d, H3'), 7.60-7.70 (m, H4'), 7.22-7.38 (m, H5'), 7.22-7.38 (m, H6'), 7.88 (d, H7').

Workup

  1. customThe mixture was reacted at 80° C. for 20 hours
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customrecrystallized from benzene/hexane

Sources & evidence

ORD record
ord-aeffd6daa87f437eb4defd0fe8a5ffd2
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

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