HCID 11459960, compound → HCID 18624494, compound

HRID 1633761Notes

Reaction equation

HRID 1633761 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[CH:10]=[CH:9][C:8]2[NH:7][C:6](=[O:11])[C:5]3=[C:14]([C:15]4[NH:16][CH:17]=[CH:18][CH:19]=4)[CH2:13][CH2:12][C:3]=1[C:4]=23

Participants

4

Reactant 1

HCID 11459960HCID 11459960, compound

Product 1

HCID 18624494HCID 18624494, 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) (50 mg, 0.184 mmol) in 1.0 N NaOH (10 mL) was heated under reflux overnight. The reaction mixture 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)-4,5-dihydro-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 42.2 mg, 90.4%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  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-1c79658ef9744a5180c44d732701454d
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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