Cesium carbonate → tert-butyl 5-(2-oxopyrrolidin-1-yl)-1H-indole-1-carboxylate

HRID 1467977

Reaktionsgleichung

Reaktionsgleichung von HRID 1467977
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5]2.[NH:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[O:23]=[C:19]1[CH2:20][CH2:21][CH2:22][N:18]1[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5]2

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 161259585-Iodo-1H-indole, N-BOC protected

Produkt 1

HCID 67616327tert-butyl 5-(2-oxopyrrolidin-1-yl)-1H-indole-1-carboxylateAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of tert-butyl 5-iodo-1H-indole-1-carboxylate (1.5 g, 4.3 mmol), Xant Phos (0.25 g, 0.43 mmol) and 2-pyrrolidinone (0.74 g, 8.7 mmol) in anhydrous dioxane (15 mL), cesium carbonate (2.8 g, 8.7 mmol) was added and the contents were stirred for 5 minutes. Tris(dibenzylideneacetone)-dipalladium (0)chloroform adduct (0.452 g, 0.437 mmol) was added and the reaction mixture was stirred at 110-115° C. for 6 h. The reaction mixture was cooled to room temperature and filtered over celite and filtrate was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to yield tert-butyl 5-(2-oxopyrrolidin-1-yl)-1H-indole-1-carboxylate (0.80 g, 61%); MS: 301 (M+1).

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction mixture was stirred at 110-115° C. for 6 h
  3. filtrationfiltered over celite and filtrate
  4. extractionwas extracted with ethyl acetate
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c76cba1980ce4fd093d34909079f1882
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000175B2

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