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

HRID 1908585Notes

Reaction equation

HRID 1908585 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 69.3%

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-trimethylsilanylethynyl-phenylamine (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 a short plug of Celite. The filter cake washed with EtOAc. The combined filtrate washed with water, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (10-20% ethyl acetate/hexane) to provide 5-tert-butyl-6-nitro-1H-indole as a yellow solid (13 g, 69%).

Workup

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

Sources & evidence

ORD record
ord-95fd044507494150a27bee67406469cd
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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