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

HRID 1594666

反応式

HRID 1594666 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 217064915-Trimethylsilylethynyl-4-methyl-3-nitro-2-pyridone収率 96.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

反応条件

温度
90 °C

実験手順

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%)

後処理

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

出典と根拠

ORDレコード
ord-308b3896a9554b94b413ee87e12cc844
出典データセット
uspto-grants-2001_09
特許番号
US06284768B1

関連ノート

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