Cesium carbonate → 6-(4-Methyl-piperazin-1-yl)-1-(toluene-4-sulfonyl)-1H-indole

HRID 1465832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465832
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.[CH3:60][N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:60][N:61]1[CH2:66][CH2:65][N:64]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])=[CH:4][CH:3]=2)[CH2:63][CH2:62]1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 11348662HCID 11348662, VerbindungHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl

Produkt 1

HCID 674572186-(4-Methyl-piperazin-1-yl)-1-(toluene-4-sulfonyl)-1H-indoleAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 250 mL round bottom flask was loaded with 6-Bromo-1-(toluene-4-sulfonyl)-1H-indole (4 g, 11.4 mmol), Cs2CO3 (7.4 g, 22.8 mmol), Pd2dba3 (0.104 g, 0.114 mmol), RuPHOS (0.106 g, 0.23 mmol), Toluene (150 mL), N-Methyl piperazine (1.9 mL, 17.2 mol), evacuated and flushed with nitrogen. Next the reaction flask was heated at 100° C., over the weekend. Analysis at this point showed that most of the starting material had converted to the product. After cooling to room temperature, the solution was diluted with EtOAc (150 mL), filtered through a pad of celite, washed with additional EtOAc (150 mL) and was evaporated. The resulting oil was chromatographed on silica gel to give the product as a thick brown oil (which crystallized on standing), 3.1 g, (73.8% yield).

Aufarbeitung

  1. customevacuated
  2. customflushed with nitrogen
  3. temperatureAfter cooling to room temperature
  4. additionthe solution was diluted with EtOAc (150 mL)
  5. filtrationfiltered through a pad of celite
  6. washwashed with additional EtOAc (150 mL)
  7. customwas evaporated
  8. customThe resulting oil was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ccba6e2f6fbc48ddbacfb2035fa5d78f
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999993B2

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