Methyl iodide → (6-Bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl ester

HRID 217209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217209
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]([N+:15]([O-:17])=[O:16])=[N:10][C:11]([Br:14])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[N:7]([C:8]1[C:9]([N+:15]([O-:17])=[O:16])=[N:10][C:11]([Br:14])=[CH:12][CH:13]=1)[CH3:21])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59227449(6-Bromo-2-nitro-pyridin-3-yl)-carbamic acid tert-butyl ester

Produkt 1

HCID 46855854(6-Bromo-2-nitro-pyridin-3-yl)-methyl-carbamic acid tert-butyl esterAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of (6-bromo-2-nitro-pyridin-3-yl)-carbamic acid tert-butyl ester (6) (290 mg, 0.91 mmol) in DMF (10 mL), NaH (57 mg, 1.36 mmol, 57% dispersion in oil) was added at 0° C. After stirring for 15 minutes, methyl iodide (79 μL, 1.27 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction mixture was then quenched with saturated ammonium chloride solution (15 mL) and extracted with ethyl acetate (2×40 mL). The combined organic extracts were washed with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography using 20% ethyl acetate in hexane to give compound (7) (268 mg) as a pale yellow solid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 1 hour
  2. customThe reaction mixture was then quenched with saturated ammonium chloride solution (15 mL)
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d367c519052e426fa2536d007284b183
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193363B2

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