HCID 10038811, compound → Methyl 5-fluoro-2-oxo-2,3-dihydro-1H-indole-3-carboxylate

HRID 1392255Notes

Reaction equation

HRID 1392255 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9](OC)=[O:10])[CH:7]=1.[H][H]>[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:17][C:9](=[O:10])[CH:8]2[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 2

HCID 10038811HCID 10038811, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22476319Methyl 5-fluoro-2-oxo-2,3-dihydro-1H-indole-3-carboxylateYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a flask made of glass equipped with a stirrer, a thermometer and a gas inlet tube and having an inner volume of 100 ml were charged 3.93 g (14.2 mmol) of dimethyl 2-(5-fluoro-2-nitrophenyl)malonate synthesized according to Example 1 with a purity of 98%, 0.5 g (0.12 mmol as a palladium atom) of 5% by weight palladium/carbon (49% hydrated product) and 50 ml of ethyl acetate under argon atmosphere. Then, the inner system was replaced with hydrogen, and the mixture was reacted under a hydrogen pressure of 0.15 MPa at 20° C. for 2 hours. After completion of the reaction, the catalyst was filtered off by filtrating the reaction mixture and then the filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography (filler: Daisogel 1002W, eluent: chloroform) to obtain 2.76 g (isolation yield: 92%) of 5-fluoro-3-methoxycarbonyloxindole as white crystals with a purity of 99% (areal percentage by high performance liquid chromatography).

Workup

  1. customIn a flask made of glass
  2. customequipped with a stirrer
  3. customsynthesized
  4. customthe mixture was reacted under a hydrogen pressure of 0.15 MPa at 20° C. for 2 hours
  5. customAfter completion of the reaction
  6. filtrationthe catalyst was filtered off
  7. filtrationby filtrating the reaction mixture
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. concentrationthe resulting concentrate
  10. customwas purified by silica gel column chromatography (filler: Daisogel 1002W, eluent: chloroform)

Sources & evidence

ORD record
ord-9e31eab5fca043e79a3f8b210f5da11b
Source dataset
uspto-grants-2008_03
Patent number
US07342040B2

Reaction notes

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