1,1'-Carbonyldiimidazole → 6-fluoro-5-(2-oxo-imidazolidin-1-yl)-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

HRID 1861005Notes

Reaction equation

HRID 1861005 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:6]=[C:7]([C:19]2[NH:20][CH:21]=[CH:22][CH:23]=2)[C:8]2[C:9](=[O:18])[NH:10][C:11]3[C:16]=2[C:15]=1[C:14]([F:17])=[CH:13][CH:12]=3.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>ClCCCl>[F:17][C:14]1[C:15]2[C:16]3[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:18])[C:8]=3[C:7]([C:19]1[NH:20][CH:21]=[CH:22][CH:23]=1)=[CH:6][C:5]=2[N:4]1[CH2:3][CH2:2][NH:1][C:24]1=[O:25]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 4477665-((2-Aminoethyl)amino)-6-fluoro-3-(1H-pyrrol-2-YL)benzo(CD)indol-2(1H)-one

Product 1

HCID 102686566-fluoro-5-(2-oxo-imidazolidin-1-yl)-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 5-(2-amino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one (from Example 9 above) (31.1 mg, 0.1 mmol) in 1,2-dichloroethane (3 mL) was added 1,1′-carbonyldiimidazole (Aldrich, 162 mg, 1.0 mmol) at room temperature. The reaction mixture was heated under reflux overnight. The reaction was then quenched with saturated aqueous sodium bicarbonate solution (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were successively washed with water (5 mL) and brine (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with ethyl acetate and hexanes, filtered, and dried to give 6-fluoro-5-(2-oxo-imidazolidin-1-yl)-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 19.5 mg, 58.0%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. customThe reaction was then quenched with saturated aqueous sodium bicarbonate solution (5 mL)
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. washThe combined organic extracts were successively washed with water (5 mL) and brine (5 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was triturated with ethyl acetate and hexanes
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-e2d9691e2366489db49498125a90fd04
Source dataset
uspto-grants-2003_03
Patent number
US06531598B1

Reaction notes

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