Indole → 1,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-one oxime

HRID 1868404

Reaktionsgleichung

Reaktionsgleichung von HRID 1868404
Br[CH2:2][C:3](=[N:8][OH:9])[C:4]([F:7])([F:6])[F:5].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.C(=O)([O-])[O-].[Na+].[Na+]>C(OC)(C)(C)C>[F:5][C:4]([F:7])([F:6])[C:3](=[N:8][OH:9])[CH2:2][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 798Indole2×HCID 10340Sodium CarbonateHCID 27822732-Propanone,3-bromo-1,1,1-trifluoro-, oxime

Produkt 1

HCID 765493791,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-one oximeAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To a solution of the 1.64 g (7.96 mmol) of 3-bromo-1,1,1-trifluoropropan-2-one oxime in 250 mL of methyl tert-butyl ether was added 3.74 g (31.92 mmol) of indole followed by 5.0 g (47.62 mmol) of powdered (freshly ground) sodium carbonate. The reaction was monitored by thin layer chromatography (ethyl acetate-hexanes (2:8)) to afford a new more polar product compared to indole (PMA-stained and UV-active). The mixture was then filtered through diatomaceous earth and concentrated in vacuo. The residue was then concentrated in vacuo and diluted first with dichloromethane (1 part) and then hexanes (4 parts) and passed through a pad of silica gel using dichloromethane-hexanes (gradient: 20%-100%) to afford 1.72 g (89.2%) of 1,1,1-trifluoro-3-(1H-indol-3-yl)propan-2-one oxime as a white solid.

Aufarbeitung

  1. customto afford a new more polar product
  2. filtrationThe mixture was then filtered through diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. concentrationThe residue was then concentrated in vacuo
  5. additiondiluted first with dichloromethane (1 part)

Quellen und Nachweise

ORD-Eintrag
ord-17a77fdf9e674e5b9d3fad3739dbfcc3
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07635711B2

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