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

HRID 73330

Reaktionsgleichung

Reaktionsgleichung von HRID 73330
[CH3:1][O:2][C:3](=[O:33])/[C:4](/[NH:22]C(OCC1C=CC=CC=1)=O)=[CH:5]/[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+].N>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]([C:4]1[NH:22][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 58437218(Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxycarbonylaminoacrylic acid methyl ester

Produkt 1

HCID 584374865-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl esterAusbeute 63,1 %

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-benzyloxycarbonylaminoacrylic 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-865e985d28cb44e48a972d7c9f48d8fb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829040B2

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