Dimethyl Sulfoxide → 1-Hexyl-4-methyl-3-nitro-5-methoxycarbonyl-2-pyridone

HRID 1594672노트

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HRID 1594672 반응식
[CH2:1]([N:7]1[CH:12]=[C:11](I)[C:10]([CH3:14])=[C:9]([N+:15]([O-:17])=[O:16])[C:8]1=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:19]([O-:22])(=[O:21])C.[K+].[CH3:24]S(C)=O>CO.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:7]1[CH:12]=[C:11]([C:19]([O:22][CH3:24])=[O:21])[C:10]([CH3:14])=[C:9]([N+:15]([O-:17])=[O:16])[C:8]1=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

7

반응물 3

HCID 679Dimethyl SulfoxideHCID 517044Potassium AcetateHCID 217065251-Hexyl-5-iodo-4-methyl-3-nitro-2-pyridone

생성물 1

HCID 217065051-Hexyl-4-methyl-3-nitro-5-methoxycarbonyl-2-pyridone수율 75%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A mixture of 1-hexyl-5-iodo-4-methyl-3-nitro-2-pyridone (0.500 g, 1.37 mmol), tris(dibenzylideneacetone)dipalladium (0.003 g), diphenylphosphinoferrocence (0.154 g) and potassium acetate (0.565 g) in DMSO (10 mL) and methanol (10 mL) was stirred and heated at 60° C. under an atmosphere of carbon monoxide for 4 hours. The mixture was diluted with ethyl acetate, washed with aqueous sodium bicarbonate, dried (MgSO4), filtered, and evaporated. Chromatography of the residue over silica gel (30% ethyl acetate/petroleum ether) gave 1-hexyl-4-methyl-3-nitro-5-methoxycarbonyl-2-pyridone (0.305 g, 75%).

후처리

  1. washwashed with aqueous sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-5bbee3a5f4814695839d10d101d8e365
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06284768B1

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