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

HRID 2267478Notes

Reaction equation

HRID 2267478 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, 0.25 mol) 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 the title compound (5.1 g) 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-c979b3c2fa884567aa6a8b92e4feedd6
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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