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

HRID 1915470Notes

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

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

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

Sources & evidence

ORD record: ord-36b99c95346b4ea1afd4198ebd4e67d7
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614327B2

Reaction notes

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