HCID 21071406, Verbindung → HCID 21071593, Verbindung

HRID 1371914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371914
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH:9]=[C:8]2[CH2:24][CH2:25][N:26]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:2][CH3:3]>CCO.O.NN>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11]([N:10]([Si:14]([CH:21]([CH3:22])[CH3:23])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:16])[CH3:17])[CH:9]=[C:8]2[CH2:24][CH2:25][NH2:26])=[CH:12][CH:13]=1)[CH2:2][CH3:3]

Komponenten

4

Edukt 1

HCID 21071406HCID 21071406, Verbindung

Produkt 1

HCID 21071593HCID 21071593, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 24654Hydrazine hydrate (1:1)Lösungsmittel

Versuchsvorschrift

Combine 2-(2-(5-propoxy-1-triisopropylsilanyl-1H-indol-3-yl)ethyl)isoindole-1,3-dione (416 mg, 0.8 mmol) in 20 mL EtOH and 1 mL hydrazine hydrate. Reflux for 3 hours, filter through celite and concentrate to residue. Dissolve the residue in 10 mL MeOH and load onto a 12 g SCX ion exchange cartridge and rinse sequentially with MeOH, DMP, then MeOH. Elute the product with 2 M NH3 in MeOH to give the title compound as an oil: ISMS 375 (M+1); 1H NMR (CDCl3) 7.34–7.32 (d, 1H), 7.02 (s, 1H), 7.00–6.99 (d, 1H), 6.80–6.77 (m, 1H), 3.97–3.94 (m, 2H), 3.01–2.98 (m, 2H), 2.86–2.83 (m, 2H), 1.88–1.76 (m 2H), 1.70–1.58 (m, 3H), 1.3 (bs, 2H), 1.14–1.08 (m, 18H), 1.06–1.02 (t, 3H).

Aufarbeitung

  1. temperatureReflux for 3 hours
  2. filtrationfilter through celite
  3. concentrationconcentrate to residue
  4. dissolutionDissolve the residue in 10 mL MeOH
  5. washload onto a 12 g SCX ion exchange cartridge and rinse sequentially with MeOH, DMP
  6. washElute the product with 2 M NH3 in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-bb2de4e5599f473d802879e110cf21d6
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157488B2

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