Ethyl Acetate → 5-Trimethylsilylethynyl-4-methyl-3-nitro-2-pyridone

HRID 1387275

Reaktionsgleichung

Reaktionsgleichung von HRID 1387275
Br[C:2]1[C:3]([CH3:12])=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=[O:8])[NH:6][CH:7]=1.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].C(OCC)(=O)C>CN(C=O)C.C(N(CC)CC)C>[CH3:13][Si:14]([C:17]#[C:18][C:2]1[C:3]([CH3:12])=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=[O:8])[NH:6][CH:7]=1)([CH3:16])[CH3:15]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 217065175-Bromo-2-hydroxy-4-methyl-3-nitropyridine

Produkt 1

HCID 217064915-Trimethylsilylethynyl-4-methyl-3-nitro-2-pyridoneAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 5-bromo-4-methyl-3-nitro-2-pyridone (1.0 g, 2.8 mmol), trimethylsilylacetylene (1.2 mL, 8.5 mmol), bis(triphenylphosphine)Pd(II) chloride (0.100 g) and cuprous iodide (0.025 g) in DMF (4 mL) and triethylamine (2 mL) was heated at 90° C. in a scaled tube for 7 hours. Ethyl acetate was added, and the mixture was washed with water, dried, filtered and evaporated. Chromatography of the residue over silica gel (40% ethyl acetate/hexane) gave 5-trimethylsilylethynyl-4-methyl-3 -nitro-2-pyridone (1.0 g, 2.7 mmol, 96%)

Aufarbeitung

  1. washthe mixture was washed with water
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-306fed1bbb784392bb1cdde265874de0
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268365B1

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