[2-(4,5-Difluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine → 5,6-Difluoro-1H-indole

HRID 1836633Notes

Reaction equation

HRID 1836633 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]=[CH:10]N(C)C)=[C:4]([N+:14]([O-])=O)[CH:3]=1>[Pd].CO>[F:8][C:7]1[CH:6]=[C:5]2[C:4](=[CH:3][C:2]=1[F:1])[NH:14][CH:10]=[CH:9]2

Participants

4

Reactant 1

HCID 73990727[2-(4,5-Difluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine

Product 1

HCID 27787325,6-Difluoro-1H-indoleYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of [2-(4,5-difluoro-2-nitro-phenyl)-vinyl]-dimethyl-amine (7.0 g, 30.7 mmol) and 10% palladium on charcoal (1.4 g) in methyl alcohol was hydrogenated in a Parr apparatus at 50 psi for 2 h and then filtered through Celite. The filtrate was concentrated in vacuo and the crude product purified by silica gel column chromatography (hexanes/ethyl acetate, 8:2) to afford 5,6-difluoroindole (1.28 g, 28%) as a yellow solid. 1H-NMR δ(400 MHz, CDCl3) 8.10 (1H, br s), 7.36 (1H, dd, J=10.7, 7.8 Hz), 7.22 (1H, t, J=2.8 Hz), 7.17 (1H, dd, J=7.4, 3.1 Hz), 6.50 (1H, m).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe crude product purified by silica gel column chromatography (hexanes/ethyl acetate, 8:2)

Sources & evidence

ORD record
ord-fb76819da7ea42c7920dd5a8f6d96643
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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