5-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid → 5-bromo-6-fluoro-1H-indole-7-carboxylic acid

HRID 387306Notes

Reaction equation

HRID 387306 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[F:11])[NH:7][CH2:6][CH2:5]2>C1COCC1.Cl.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:12]([OH:14])=[O:13])[C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 1

HCID 593326645-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid

Product 1

HCID 593327305-bromo-6-fluoro-1H-indole-7-carboxylic acidYield 61.7%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-bromo-6-fluoro-2,3-dihydro-1H-indole-7-carboxylic acid (5.8 g, 0.022 mol) in THF (120 mL) was added MnO2 (11.6 g, 0.134 mol). The reaction mixture was stirred at reflux overnight and then filtered (hot) through celite, washing with hot THF (2×75 mL). The filtrate was concentrated, giving a brown solid, which was suspended in 1M HCl (150 mL). The mixture stirred at reflux overnight to remove traces of Mn and then cooled to room temperature. The solid was filtered off, dried, and recrystallised from IPA, giving 3.5 g (61%) of the title compound.

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered (hot) through celite
  3. washwashing with hot THF (2×75 mL)
  4. concentrationThe filtrate was concentrated
  5. customgiving a brown solid, which
  6. stirringThe mixture stirred
  7. temperatureat reflux overnight
  8. customto remove traces of Mn
  9. filtrationThe solid was filtered off
  10. customdried
  11. customrecrystallised from IPA

Sources & evidence

ORD record
ord-e454036211f046d8979dc2edad596eef
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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