Water → 1-(6-Chloro-5-fluoroindol-1-yl)-2-ethylamine

HRID 392094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 392094
[OH-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][C:5]=1[F:13].Cl.Cl[CH2:16][CH2:17][NH2:18].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:16][CH2:17][NH2:18])=[CH:6][C:5]=1[F:13]

Komponenten

7

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27736486-Chloro-5-fluoro-1H-indoleHCID 97937372-Chloroethylamine hydrochloride

Produkt 1

HCID 189862171-(6-Chloro-5-fluoroindol-1-yl)-2-ethylamineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Tetra-n-butylammonium hydrogensulfate (0.1 g, 0.33 mmol), powdered sodium hydroxide (1.3 g, 33 mmol) and 6-chloro-5-fluoroindole (1.4 g, 8.3 mmol) were stirred at room tempera in acetonitrile (40 mL) for 1 h. 2-Chloroethylamine hydrochloride (1.45 g, 12.5 mmol) was then added in 1 portion and the reaction was heated to reflux and stirred for 36 h. After allowing to cool to room temperature the mixture was poured into water (100 mL) and extracted with ethyl acetate (3×70 mL). The combined organic extracts were washed with brine (1×100 mL), dried (magnesium sulfate), filtered and the solvent removed under vacuo to leave a crude oil. The oil was purified by flash column chromatography [SiO2; ethyl acetate-methanol-ammonium hydroxide, (90:9:1)] to give the product as an orange oil (1.4 g, 80%). IR νmax (film)/cm−1 3377, 3104, 2937, 2868, 1675, 1568, 1505, 1479, 1449, 1400, 1357, 1327, 1291, 1236, 1143, 1090, 1030, 994, 862, 817, 753, 717, 698, 678, 646, 633, 596 and 579; NMR δH (400 MHz; DMSO-d6) 7.79 (1H, d, J 7 Hz), 7.51 (1H, d, J 10 Hz), 7.50 (1H, d, J 3.5 Hz), 6.46 (1H, m), 4.13 (2H, t, J 6.3 Hz), 2.86 (2H, t, J 6.3 Hz), 1.52 (1H, br. s).

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux
  3. extractionextracted with ethyl acetate (3×70 mL)
  4. washThe combined organic extracts were washed with brine (1×100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customthe solvent removed under vacuo
  8. customto leave a crude oil
  9. customThe oil was purified by flash column chromatography [SiO2; ethyl acetate-methanol-ammonium hydroxide, (90:9:1)]

Quellen und Nachweise

ORD-Eintrag
ord-ee3dffba2e4e4d8a9be055add0babc5f
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800627B1

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