Toluene → HCID 178527321, Verbindung

HRID 38839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38839
[C:1]([C:3]1[CH:11]=[C:10]([C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH:14]=[CH:15][N:16]3C(OC(C)(C)C)=O)[CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][N:7]2[S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29])#[N:2].C1(C)C=CC=CC=1.C([Sn](CCCC)=O)CCC.C[Si]([N:58]=[N+:59]=[N-:60])(C)C>O.C(O)(=O)C>[NH:16]1[C:17]2[C:13](=[C:12]([C:10]3[CH:9]=[C:8]4[C:4]([CH:5]=[N:6][N:7]4[S:28]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)(=[O:29])=[O:30])=[C:3]([C:1]4[NH:2][N:60]=[N:59][N:58]=4)[CH:11]=3)[CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:15]1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 667768451,1-Dimethylethyl 4-[4-cyano-1-(phenylsulfonyl)-1H-indazol-6-yl]-1H-indole-1-carboxylate

Produkt 1

HCID 178527321HCID 178527321, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a round bottomed flask was charged 1,1-dimethylethyl 4-[4-cyano-1-(phenylsulfonyl)-1H-indazol-6-yl]-1H-indole-1-carboxylate (6.16 g, 12.36 mmol) followed by toluene (250 ml). The resulting solution was then treated with dibutyl(oxo)stannane (0.554 g, 2.224 mmol) and trimethylsilyl azide (3.3 ml, 25.09 mmol). The mixture was heated to 90° C. overnight, then cooled to room temperature and concentrated in vacuo. The residue was dissolved in methanol/DCM and preabsorbed onto silica (20 g). This was placed on the top of a silica cartridge (750 g) and eluted with 0-40% methanol in DCM. The product containing fraction was evaporated to give a green foam which was placed into acetic acid (50 ml) and the mixture heated to 100° C. overnight. The mixture was heated for a further 24 h, then cooled to room temperature and water (250 ml) added. A precipitate formed, which was collected by filtration and air dried over the weekend to give the title compound as a pale grey solid (1.8 g).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in methanol/DCM
  4. custompreabsorbed onto silica (20 g)
  5. washeluted with 0-40% methanol in DCM
  6. additionThe product containing fraction
  7. customwas evaporated
  8. customto give a green foam which
  9. temperaturethe mixture heated to 100° C. overnight
  10. temperatureThe mixture was heated for a further 24 h
  11. temperaturecooled to room temperature
  12. customA precipitate formed
  13. filtrationwhich was collected by filtration and air
  14. customdried over the weekend

Quellen und Nachweise

ORD-Eintrag
ord-3e50c8fbdcbb48278b27b3280cb48c26
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524751B2

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