Oxygen → 5-bromo-7-chloro-1H-indole

HRID 1976786Notes

Reaction equation

HRID 1976786 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][CH2:6][CH2:5]2.O=O>CO.C1C=C(C=NCCN=CC2C([O-])=CC=CC=2)C([O-])=CC=1.[Co+2]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 977OxygenHCID 167891645-Bromo-7-chloroindoline

Product 1

HCID 107281945-bromo-7-chloro-1H-indoleYield 88.3%

Reagents, catalysts & solvents 2

HCID 26517SalcomineCatalystHCID 887MethanolSolvent

Procedure

A mixture of Example 65B (0.120 g, 0.55 mmol) and salcomine (0.022 g, 0.06 mmol) in methanol (30 mL) was treated with oxygen over 18 hours and concentrated. The concentrate was purified by flash column chromatography on silica gel to provide 0.112 g of the desired product. MS (ESI(+)) m/z 232 (M+2) and 248 (M+NH4)+;

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b8bc82664f4b4f9c83a2081e443a777b
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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