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

HRID 1005405

Reaction equation

HRID 1005405 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

HCID 217064915-Trimethylsilylethynyl-4-methyl-3-nitro-2-pyridoneYield 96.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

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 sealed 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%)

Workup

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

Sources & evidence

ORD record
ord-c9f1bf0a91384fa1b2adf3e397b54aee
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Linked notes

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