1-[-2-(3-Benzyloxy-6-bromo-2-nitro-phenyl)-vinyl]-pyrrolidine → 7-(Benzyloxy)-4-bromo-1H-indole

HRID 1159824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159824
[CH2:1]([O:8][C:9]1[C:10]([N+:23]([O-])=O)=[C:11]([CH:16]=[CH:17]N2CCCC2)[C:12]([Br:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[C:11]2[C:10]=1[NH:23][CH:17]=[CH:16]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 866182601-[-2-(3-Benzyloxy-6-bromo-2-nitro-phenyl)-vinyl]-pyrrolidine2×

Produkt 1

HCID 114608287-(Benzyloxy)-4-bromo-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

1-[-2-(3-Benzyloxy-6-bromo-2-nitro-phenyl)-vinyl]-pyrrolidine (10 g, 24.8 mmol; Intermediate 82) suspended in HOAc (25 mL) was added to a boiling mixture of iron (4.15 g, 74.4 mmol) in HOAc. After 2 h boiling TLC indicated that no starting material is left. The reaction mixture was filtered while still warm. The residue was evaporated and dissolved in toluene. The toluene slurry was applied to a silica column and eluted with toluene/hexane 1/1. Obtained 3.1 g. MS (ESI+) for C15H12BrNO m/z 302, 304 (M+H)+.

Aufarbeitung

  1. waitis left
  2. filtrationThe reaction mixture was filtered
  3. temperaturewhile still warm
  4. customThe residue was evaporated
  5. dissolutiondissolved in toluene
  6. washeluted with toluene/hexane 1/1
  7. customObtained 3.1 g

Quellen und Nachweise

ORD-Eintrag
ord-d4dccfae83cf45858a017fcacec8131b
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812017B2

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