1-Methyl-1H-indole-3-carbaldehyde → HCID 58779044, Verbindung

HRID 1372757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372757
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[CH:4]=1)=[O:2].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:16]([F:25])[C:15]=1O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CO>[F:25][C:16]1[C:15]2[O:2][C:1]([C:3]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]([CH3:12])[CH:4]=3)=[N:13][C:14]=2[CH:19]=[CH:18][C:17]=1[CH2:20][C:21]([O:23][CH3:24])=[O:22]

Komponenten

5

Edukt 3

HCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 12217721Iodo benzene diacetateHCID 17859032Methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate

Produkt 1

HCID 58779044HCID 58779044, VerbindungAusbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In methanol (50 ml), 3-formyl-1-methylindole (796 mg, 5.0 mmol), methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate (1.0 g, 5.0 mmol) and Molecular Sieves 4A (10 g) were stirred at room temperature for 5 hours and then, at 70° C. for 3 hours. The reaction mixture was cooled to room temperature and iodobenzene diacetate (5.0 mmol) was added thereto. After stirring at room temperature for 14 hours, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3/1) eluate fractions, methyl 7-fluoro-2-(1-methyl-3-indolyl)-6-benzoxazolylacetate (860 mg, including impurities) was obtained as a pale brown solid. The compound was provided for the subsequent reaction without further purification.

Aufarbeitung

  1. distillationthe reaction mixture was distilled under reduced pressure
  2. customto remove the solvent
  3. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3/1) eluate fractions

Quellen und Nachweise

ORD-Eintrag
ord-99c7543ef46a426badce607a261086ba
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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