Methyl 5-bromoindoline-7-carboxylate → methyl 5-bromo-1H-indole-7-carboxylate

HRID 656005Notes

Reaction equation

HRID 656005 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[NH:7][CH2:6][CH2:5]2>O1CCCC1.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 49758858Methyl 5-bromoindoline-7-carboxylate

Product 1

HCID 24728848methyl 5-bromo-1H-indole-7-carboxylateYield 80.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-bromo-2,3-dihydro-1H-indole-7-carboxylate (6.5 g, 25 mmol) was dissolved in tetrahydrofuran (100 mL). Activated manganese dioxide (5 μm particle size, 22 g, 250 mmol) was added and the mixture stirred at room temperature for 16 hours. A further 22 g of activated manganese dioxide was added and the reaction stirred for 96 hours. The reaction was then filtered through celite and concentrated in vacuo to give 5.1 g (80%) of the title compound as a beige solid.

Workup

  1. stirringthe reaction stirred for 96 hours
  2. filtrationThe reaction was then filtered through celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92feb91ec1944631b25b642e80d6f1d2
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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