HCID 11459960, compound → HCID 9837883, compound

HRID 1633762Notes

Reaction equation

HRID 1633762 reaction equation
[F:1][C:2]1[C:3]([CH2:12][CH2:13][C:14](=O)[C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2>[OH-].[Na+].O>[F:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]=3[C:14]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)=[CH:13][CH:12]=2

Participants

4

Reactant 1

HCID 11459960HCID 11459960, compound

Product 1

HCID 9837883HCID 9837883, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 5-fluoro-4-[3-oxo-3-(1H-pyrrol-2-yl)-propyl]-1,3-dihydro-indol-2-one (from Example 5 above) (20 mg, 0.073 mmol) in 1.0 N NaOH (10 mL) was heated under reflux for 2.5 days. The reaction was diluted with water (20 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were successively washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 16.5 mg, 89.0%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 days
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were successively washed with water (10 mL) and brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-80c32d7f72cb4d96b4cad59b7d868411
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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