HCID 68460100, compound → 6-Nitro-5-(trifluoromethyl)-1H-indole

HRID 1805128Notes

Reaction equation

HRID 1805128 reaction equation
[N+:1]([C:4]1[C:5]([C:17]([F:20])([F:19])[F:18])=[CH:6][C:7]([C:11]#[C:12][Si](C)(C)C)=[C:8]([CH:10]=1)[NH2:9])([O-:3])=[O:2]>CN(C=O)C.[Cu]I>[N+:1]([C:4]1[CH:10]=[C:8]2[C:7]([CH:11]=[CH:12][NH:9]2)=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18])([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 68460100HCID 68460100, compound

Product 1

HCID 593172256-Nitro-5-(trifluoromethyl)-1H-indoleYield 31%

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 5-nitro-4-(trifluoromethyl)-2-((trimethylsilyl)ethynyl)aniline (6.0 g, 19.85 mmol) in DMF (30 mL) was added CuI (1.9 g, 9.976 mmol) under an atmosphere of nitrogen. The reaction mixture was heated at 135° C. in a sealed pressure flask overnight. The reaction mixture was then filtered and the filtrate was washed with water, dried over Na2SO4 and concentrated. The crude product was purified by silica gel column chromatography (5 to 20% EtOAc in petroleum as eluant) to obtain 6-nitro-5-(trifluoromethyl)-1H-indole (1.4 g, 31%). 1H NMR (400 MHz, CDCl3): δ 8.83 (br s, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 7.58-7.57 (m, 1H), 6.80-6.79 (m, 1H); 19F NMR (282.4 MHz, CDCl3): δ-57.82; MS (ESI): m/z [M−H]− 229.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washthe filtrate was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel column chromatography (5 to 20% EtOAc in petroleum as eluant)

Sources & evidence

ORD record
ord-9452f714329b47eb9a5f561bc020cb38
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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