Ammonia → 5-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl ester

HRID 1258187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258187
[CH3:1][O:2][C:3](=[O:33])/[C:4](/OCC1C=CC=CC=1)=[C:5](/N=C=O)\[C:6]1[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([CH3:20])=[CH:8][C:7]=1Br.C([O-])(=O)C.[Cs+].[NH3:39]>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]([C:4]1[NH:39][C:7]2[C:6]([CH:5]=1)=[CH:11][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:9]([CH3:20])[CH:8]=2)=[O:33]

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 5152919Cesium acetateHCID 86657627(Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxy-carbonylaminoacrylic acid methyl ester

Produkt 1

HCID 584374865-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of (Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxy-carbonylaminoacrylic acid methyl ester (0.2 g) and copper (I) iodide (0.075 g) in dimethylsulfoxide (8 mL) was added cesium acetate (0.38 g) at room temperature and this mixture was stirred under argon atmosphere at 90° C. for 5 hours. To this reaction mixture was added aqueous ammonia solution (28%) and the precipitated solid was collected by filtration, and washed with water, dried under reduced pressure to give the title compound (0.073 g).

Aufarbeitung

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-195a60ee40e64c0ea3151fd016263c1d
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466152B2

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