HCID 66676088, compound → 5-tert-butyl-6-nitro-1H-indole

HRID 1931318Notes

Reaction equation

HRID 1931318 reaction equation
[C:1]([C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([NH:14][C:15]#[C:16][Si](C)(C)C)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C.[Cu]I>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:14][CH:15]=[CH:16]2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 66676088HCID 66676088, compound

Product 1

HCID 574702075-tert-butyl-6-nitro-1H-indoleYield 68.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of 4-tert-butyl-5-nitro-2-trimethylsilanylethynylphenylamine (25 g, 86 mmol) in DMF (100 mL) was added CuI (8.2 g, 43 mmol) under a nitrogen atmosphere. The mixture was heated at 135° C. in a sealed pressure flask overnight, cooled down to room temperature and filtered through Celite®. The filter cake was washed with EtOAc. The combined filtrate was washed with water, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (10-20% EtOAc/Hexane) to provide 5-tert-butyl-6-nitro-1H-indole as a yellow solid (12.9 g).

Workup

  1. temperaturecooled down to room temperature
  2. filtrationfiltered through Celite®
  3. washThe filter cake was washed with EtOAc
  4. washThe combined filtrate was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (10-20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-058bdbcd2f9c40188af22878d1ac4b4f
Source dataset
uspto-grants-2012_05
Patent number
US08188283B2

Reaction notes

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