Cesium carbonate → HCID 58170499, Verbindung

HRID 1619108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619108
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:20]=[CH:19][C:11]([N:12]([CH2:16][CH2:17]I)[CH2:13][CH2:14]I)=[CH:10][CH:9]=1.[Br:21][C:22]1[CH:30]=[C:29]2[C:25]([CH2:26][C:27](=[O:38])[N:28]2C(OC(C)(C)C)=O)=[CH:24][CH:23]=1>CN(C=O)C.O>[Br:21][C:22]1[CH:30]=[C:29]2[NH:28][C:27](=[O:38])[C:26]3([CH2:17][CH2:16][N:12]([C:11]4[CH:19]=[CH:20][C:8]([Cl:7])=[CH:9][CH:10]=4)[CH2:13][CH2:14]3)[C:25]2=[CH:24][CH:23]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 58154275Tert-butyl 6-bromo-2-oxoindoline-1-carboxylateHCID 58170503HCID 58170503, Verbindung

Produkt 1

HCID 58170499HCID 58170499, VerbindungAusbeute 17,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Cesium carbonate (2.09 g, 6.4 mmol) was added in portions over 5 mins to a solution of 4-chloro-N,N-bis(2-iodoethyl)aniline (preparation 14c, 0.73 g, 1.68 mmol) and tert-butyl 6-bromo-2-oxoindoline-1-carboxylate (preparation 8a, 0.50 g, 1.60 mmol) in N,N′-dimethylformamide (20 mL) was added and the mixture was stirred for 48 hours. The mixture was diluted with water and extracted with ethyl acetate and the organic layer was washed with water, brine, dried (MgSO4) and evaporated. The residue was taken up in 1,4-dioxane (15 mL) and 5M aqueous hydrochloric acid (5 mL) and the mixture was stirred and heated to 70° C. After 30 minutes, the mixture was evaporated and partitioned between ethyl acetate and 2M aqueous hydrochloric acid. The organic layer was combined with an insoluble solid which separated and the mixture was evaporated. The residue was purified by flash chromatography (3:1 hexanes/ethyl acetate) to give the title compound (0.11 g, 17%) as a pink solid.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. stirring5M aqueous hydrochloric acid (5 mL) and the mixture was stirred
  7. waitAfter 30 minutes
  8. customthe mixture was evaporated
  9. custompartitioned between ethyl acetate and 2M aqueous hydrochloric acid
  10. customseparated
  11. customthe mixture was evaporated
  12. customThe residue was purified by flash chromatography (3:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-91ffe0e618b747e7ab44c9e231acddd8
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772288B2

Notizen zur Reaktion

Wird geladen…