Methyl morpholine oxide → HCID 86654435, Verbindung

HRID 1909899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909899
[C:1]([C:5]1[N:6]([C:18]([OH:20])=[O:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([Br:14])=[C:9]([Cl:15])[C:8]=2[CH2:16]Br)([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:25]CC1>C(#N)C>[C:1]([C:5]1[N:6]([C:18]([OH:20])=[O:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([Br:14])=[C:9]([Cl:15])[C:8]=2[CH:16]=[O:25])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 82029Methyl morpholine oxideHCID 67255556HCID 67255556, Verbindung

Produkt 1

HCID 86654435HCID 86654435, VerbindungAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of tert-butyl 5-bromo-7-(bromomethyl)-6-chloro-1H-indole-1-carboxylic acid (7.2 g) and acetonitrile (50 mL) was added 4-methyl morpholine-4-oxide (2.7 g) at room temperature. The reaction mixture was stirred at 50° C. for 7 hours and then at 70° C. overnight. The reaction mixture was concentrated under reduced pressure, ethyl acetate and water were added thereto, and a liquid-separation operation was carried out. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10) to obtain tert-butyl 5-bromo-6-chloro-7-formyl 1H-indole-1-carboxylic acid (2.9 g).

Aufarbeitung

  1. customat 70° C.
  2. customovernight
  3. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate and water
  4. additionwere added
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10)

Quellen und Nachweise

ORD-Eintrag
ord-e250af7649df42639e7d9b5de7d8657b
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598355B2

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