5-Bromo-4,6-difluoroindoline → 5-bromo-4,6-difluoro-1H-indole

HRID 338229Notes

Reaction equation

HRID 338229 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH2:6][CH2:5]2>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 838958425-Bromo-4,6-difluoroindoline

Product 1

HCID 680549995-bromo-4,6-difluoro-1H-indoleYield 100.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 5-bromo-4,6-difluoroindoline (3.6 g, 15.4 mmol) in chloroform (150 mL) was added manganese dioxide (5.3 g, 61 mmol) at room temperature/. The mixture was heated to reflux temperature for 2 hours then cooled to room temperature. The reaction was filtered and the filtrate was concentrated in vacuo. Flash column chromatography was then used to provide the title compound (3.6 g, yield 100%) as brown solid. MS (ES+): 232.0 (M+H). 1H NMR (CDCl3, 400 MHz): δ 8.27 (br. s, 1H), 7.19 (m, 1H), 7.02 (d, 1H), 6.61 (m, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature for 2 hours
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-656e711e66164152af013f09b8a1ac63
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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