4-Bromo-2-nitroaniline → 4-(3-Dimethylamino-prop-1-ynyl)-2-nitro-phenylamine

HRID 58158

Reaktionsgleichung

Reaktionsgleichung von HRID 58158
Br[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH3:12][N:13]([CH3:17])[CH2:14][C:15]#[CH:16]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:12][N:13]([CH3:17])[CH2:14][C:15]#[C:16][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Komponenten

5

Edukt 2

HCID 701324-Bromo-2-nitroanilineHCID 81643N,N-Dimethylpropargylamine

Produkt 1

HCID 1180246144-(3-Dimethylamino-prop-1-ynyl)-2-nitro-phenylamineAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of 4-bromo-2-nitro-phenylamine (1.08 g, 5 mmol) and dimethyl-prop-2-ynyl-amine (1.0 g, 12 mmol) in TEA (20 mL) was added Pd(PPh3)2Cl2 (0.7 g, 1 mmol) and CuI (360 g, 2 mmol). The solution was stirred at 60° C. under nitrogen for 3 hours. The solution was evaporated with silica gel and purified by flash chromatography on silica to give the title compound (1.1 g, 70% purity). The title compound was taken directly to the next step without further purification. MS (ESI) 221 [M+H]+.

Aufarbeitung

  1. customThe solution was evaporated with silica gel
  2. custompurified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-7785647e4fe445b2be9d75300737977f
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434697B2

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