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

HRID 1594666

반응식

HRID 1594666 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

반응 조건

온도
90 °C

실험 절차

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%)

후처리

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

출처 및 근거

ORD 기록
ord-308b3896a9554b94b413ee87e12cc844
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06284768B1

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