m-Chloroperbenzoic acid → 1-Acetyl-4-bromoindolin-3-one

HRID 2060914Notes

Reaction equation

HRID 2060914 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([Br:13])[CH:9]=[CH:10][CH:11]=2)[C:6](C=O)=[CH:5]1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([Br:13])[CH:9]=[CH:10][CH:11]=2)[C:6](=[O:24])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 534157881-Acetyl-4-bromo-1H-indole-3-carbaldehyde

Product 1

HCID 532432881-Acetyl-4-bromoindolin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Acetyl-4-bromo-1H-indole-3-carbaldehyde (3.5 g, 13.2 mmol) was dissolved in CH2Cl2 (50 mL). 3-Chloroperbenzoic acid (3.9 g, 15.8 mmol) was added, and the reaction stirred 16 h at r.t. The solution was washed with sat. NaHCO3 and brine, dried (MgSO4), and concentrated. The residue was stirred with K2CO3 (100 mg) in MeOH (50 mL) for 2 min. The solution was concentrated and purified by silica gel chromatography (100% CH2Cl2) to provide the title compound as a faintly blue solid (880 mg, 26%). MS (ES) [m+H] calc'd for C10H8BrNO2, 254, 256; found 254, 256.

Workup

  1. washThe solution was washed with sat. NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. stirringThe residue was stirred with K2CO3 (100 mg) in MeOH (50 mL) for 2 min
  5. concentrationThe solution was concentrated
  6. custompurified by silica gel chromatography (100% CH2Cl2)

Sources & evidence

ORD record
ord-10a9ec38225147eb9d1c25605d57c49b
Source dataset
uspto-grants-2012_10
Patent number
US08278450B2

Reaction notes

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