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

HRID 1633780Notes

Reaction equation

HRID 1633780 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′-carbonyidiimidazole (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-df4a232b24694220ad4e16342976d3a3
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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