Triethylsilane → methyl (4-nitro-2,3-dihydro-1H-indol-3-yl)-acetate

HRID 1094096

Reaktionsgleichung

Reaktionsgleichung von HRID 1094096
C([SiH](CC)CC)C.[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13]([C:20](=O)[C:21]([O:23][CH3:24])=[O:22])=[CH:14][NH:15]2)([O-:10])=[O:9]>C(O)(C(F)(F)F)=O>[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:14][NH:15]2)([O-:10])=[O:9]

Komponenten

4

Edukt 2

HCID 12052TriethylsilaneHCID 10243717Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

Produkt 1

HCID 10243182methyl (4-nitro-2,3-dihydro-1H-indol-3-yl)-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Triethylsilane (13 mL, 80.6 mmol) was added to a solution of methyl (4-nitro-1H-indol-3-yl)(oxo)acetate from Step A (1.00 g, 4.03 mmol) in TFA (15 mL). After 3 h, the reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with a gradient of CHCl3:MeOH—100:0 to 98:2, to give the title compound. MS: m/z=237 (M+1).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a gradient of CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-52efd6ecdbe343a7943f485fd693789b
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133891B2

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