Acetic Acid → HCID 58154281, Verbindung

HRID 1619102Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619102
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][C:13](=[O:24])[N:14]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:10][CH:9]=1.I[CH2:26][CH2:27][O:28][CH2:29][CH2:30]I.C(O)(=O)C>CN(C=O)C.O.C(OCC)(=O)C>[Br:7][C:8]1[CH:16]=[C:15]2[N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:13](=[O:24])[C:12]3([CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:11]2=[CH:10][CH:9]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 34307791-Iodo-2-(2-iodoethoxy)ethaneHCID 58154275Tert-butyl 6-bromo-2-oxoindoline-1-carboxylate

Produkt 1

HCID 58154281HCID 58154281, VerbindungAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Cesium carbonate (20.7 g, 63.5 mmol) was added portionwise over a 20 minute period to a stirred solution of tert-butyl 6-bromo-2-oxoindoline-1-carboxylate (preparation 8a, 6.0 g, 16.0 mmol) and 1-iodo-2-(2-iodoethoxy)ethane (6.58 g, 17.6 mmol) in N,N′-dimethylformamide (250 mL) at −20° C. under an argon atmosphere. After the addition the mixture was warmed to room temperature and stirred for 3 hours. Acetic acid (1.1 mL) followed by ethyl acetate and water were added to the reaction mixture and the organic layer was separated, washed with water, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (10:1 to 5:1 hexanes/ethyl acetate) gave the title compound (4.50 g, 61%) as a pale yellow solid.

Aufarbeitung

  1. additionAfter the addition the mixture
  2. additionwere added to the reaction mixture
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification of the residue by flash chromatography (10:1 to 5:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-36f2481eb1d040969945856d40836e72
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772288B2

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