Methyl iodide → Methyl 5-bromo-3-(cyclohexyl(methyl)amino)-2-methylbenzoate

HRID 1530216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530216
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:20](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:20])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 70872336Methyl 5-bromo-3-(cyclohexylamino)-2-methylbenzoate

Produkt 1

HCID 70872437Methyl 5-bromo-3-(cyclohexyl(methyl)amino)-2-methylbenzoateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of methyl 5-bromo-3-(cyclohexylamino)-2-methylbenzoate (2.75 g, 8.45 mmol) in acetonitrile (25 mL), cesium carbonate (5.45 g, 16.9 mmol) and methyl iodide (6 g, 42.3 mmol) were added; resulting solution was heated at 80° C. for 20 h. On completion, the solution was cooled to room temperature and filtered, and the residue was washed with ethyl acetate. The filtrate was concentrated and then purified by column chromatography to afford methyl 5-bromo-3-(cyclohexyl(methyl)amino)-2-methylbenzoate (2.5 g, 87%).

Aufarbeitung

  1. temperatureOn completion, the solution was cooled to room temperature
  2. filtrationfiltered
  3. washthe residue was washed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-de8e67738bbc4c67b06d4eac27d3489f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090562B2

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