Pyrrole → HCID 67691303, compound

HRID 1939987Notes

Reaction equation

HRID 1939987 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[CH:17]=[CH:16][CH:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[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

Participants

5

Reactant 3

HCID 8027PyrroleHCID 11430Potassium CarbonateHCID 109017203-Iodo-4H-chromen-4-one

Product 1

HCID 67691303HCID 67691303, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an eggplant type flask (25 ml), 3-iodochromone (136 mg) prepared in Example 1, pyrrol (134 mg), potassium carbonate (1382 mg), and dimethylformamide (15 ml) were added and 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 purified by the silica gel column chromatography, and the purified product was recrystallized from benzene/hexane to give the titled compound (59.9 mg; yield=56.4%) as light ocher crystals. Melting point: 134°-135 ° C. 1H-NMR(CDCl3, δ ppm): 6.31 (s ,H3), 8.22 (dd, H5), 7.41-7.54 (m, H6), 7.70 (t, H7), 7.41-7.54 (m, H8), 7.32 (br. t, H2'), 6.44(br. t, H3'), 6.44(br. t, H4'), 7.32(br. t, H5').

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

Sources & evidence

ORD record
ord-c9946120ae084394a7f80067650ac44d
Source dataset
uspto-grants-1997_12
Patent number
US05698575

Reaction notes

Loading…