N-bromobutanimide → 1-BOC-5-bromomethyl-7-nitro-indole-2-carboxylic acid methyl ester

HRID 1045843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1045843
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[N+:15]([O-:17])=[O:16])=[O:4].[Br:25]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14][Br:25])=[CH:9][C:8]=2[N+:15]([O-:17])=[O:16])=[O:4]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 595429701-BOC-5-methyl-7-nitro-indole-2-carboxylic acid methyl ester

Produkt 1

HCID 594480901-BOC-5-bromomethyl-7-nitro-indole-2-carboxylic acid methyl esterAusbeute 114,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-BOC-5-methyl-7-nitro-indole-2-carboxylic acid methyl ester (34 g, 101.7 mmol) prepared in Step A was dissolved in carbon tetrachloride (100 mL). N-bromosuccinimide (27.2 g, 152.6 mmol) and AIBN (1.7 g, 10.2 mmol) were added thereto, and the mixture was stirred for 5 h at 80° C. After completion of the reaction, the reaction mixture was distilled under reduced pressure, and purified by column chromatography to give the title compound (48.0 g, Yield 100%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. distillationthe reaction mixture was distilled under reduced pressure
  3. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-847bff87140b4607a7b5faac278126d3
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569307B2

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