4-Hydroxymethylpyridine → ethyl 5-fluoro-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylate

HRID 1097254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097254
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23]2.[N:34]1[CH:39]=[CH:38][C:37]([CH2:40]O)=[CH:36][CH:35]=1>C1(C)C=CC=CC=1>[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH2:40][C:37]1[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=1)[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23]2

Komponenten

5

Edukt 3

HCID 114724-HydroxymethylpyridineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylate

Produkt 1

HCID 15978981ethyl 5-fluoro-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylateAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 5.5 g (21.72 mmol) of 1,1′-azodicarbonyl-dipiperidine, in solution in 15 ml of dry toluene, is added, under argon at 20° C., dropwise, to a solution of 3 g (14.48 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 2.37 g (21.72 mmol) of 4-pyridylcarbinol and 5.45 ml (21.72 mmol) of n-tributylphosphine in 200 ml of toluene. The mixture is stirred at 20° C. for 48 h. The reaction mixture is subsequently concentrated under reduced pressure. The residue is purified by silica column chromatography (eluent: heptane/ethyl acetate). 3.2 g of the expected product are thus isolated, which product is used as it is in the subsequent synthesis.

Aufarbeitung

  1. concentrationThe reaction mixture is subsequently concentrated under reduced pressure
  2. customThe residue is purified by silica column chromatography (eluent: heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c92795dc8c2d45d1a1b10dd8956f8ed7
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143248B2

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