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

HRID 1054572Notes

Reaction equation

HRID 1054572 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, 1 H), 7.19 (m, 1 H), 7.02 (d, 1 H), 6.61 (m, 1 H).

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-593a0a10c1134ee09b758c37f8b02dce
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

Loading…