Benzonitrile → 5-Methyl-3,6-diphenyl-5H-isoxazolo[4,3-c]pyridin-4-one

HRID 8310

反応式

HRID 8310 の反応式
[CH3:1][NH:2][C:3]([C:5]1[C:6]([CH3:16])=[N:7][O:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4].C([Li])CCC.[C:22](#N)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH3:1][N:2]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:16][C:6]2=[N:7][O:8][C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:5]2[C:3]1=[O:4]

参加物

5

反応物 3

HCID 7505BenzonitrileHCID 666631943-Methyl-5-phenyl-isoxazole-4-carboxylic acid methylamideHCID 178418339Butyllithium

生成物 1

HCID 220155655-Methyl-3,6-diphenyl-5H-isoxazolo[4,3-c]pyridin-4-one収率 48.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

159 mg (0.73 mmol) of 3-methyl-5-phenyl-isoxazole-4-carboxylic acid methylamide is suspended in 4 ml of THF under argon. At −5° C. a solution of butyl lithium (1.0 ml, 1.6M in hexane, 1.6 mmol, 2.2 eq.) is slowly added. After 1 h at this temperature, the solution is warmed to 0° C. and 0.92 ml (0.88 mmol, 1.2 eq.) of benzonitrile is slowly added. Under warming to room temperature, the red solution is stirred for another 2 h, then quenched with 0.1 ml of water and concentrated. The residue is then taken up in 4 ml of a 4M solution of HCl in dioxane and the suspension stirred for 16 h at room temperature. Then, the solvent is removed and the residue dissolved in ethyl acetate and carefully neutralised with sat. NaHCO3-solution. The phases are separated and the organic phases washed with brine, dried over Na2SO4 and concentrated. Chromatographic purification (hexane/ethyl acetate 90:10) yields 108 mg (48%) of 5-methyl-3,6-diphenyl-5H-isoxazolo[4,3-c]pyridin-4-one as a white solid. Mass spectrum: m/z (M+H)+: 303.2

後処理

  1. temperatureUnder warming to room temperature
  2. customquenched with 0.1 ml of water
  3. concentrationconcentrated
  4. stirringthe suspension stirred for 16 h at room temperature
  5. customThen, the solvent is removed
  6. dissolutionthe residue dissolved in ethyl acetate
  7. customThe phases are separated
  8. washthe organic phases washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customChromatographic purification (hexane/ethyl acetate 90:10)

出典と根拠

ORDレコード
ord-0e553ab04cd04660a202ef9b4f2450c0
出典データセット
uspto-grants-2006_08
特許番号
US07087756B2

関連ノート

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