Methyl iodide → n-(6-Bromo-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-n-methyl-2-methyl benzoic acid amide

HRID 552629ノート

反応式

HRID 552629 の反応式
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:34])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=4)([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=3)=[CH:12][C:11]=2[CH3:33])[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH3:39]I>CN(C)C=O>[Br:1][C:2]1[N:7]=[C:6]([N:8]([CH3:39])[C:9](=[O:34])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:20][C:19]([C:25]4[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=4)([C:21]([F:23])([F:24])[F:22])[O:18][N:17]=3)=[CH:12][C:11]=2[CH3:33])[CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86654454N-(6-bromo-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl benzoic acid amideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86654455n-(6-Bromo-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-n-methyl-2-methyl benzoic acid amide収率 76.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a solution of 0.23 g of N-(6-bromo-2-pyridyl)-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-yl]-2-methyl benzoic acid amide in 5 mL of N,N-dimethylformamide, 0.02 g of 55% oily sodium hydride was added at room temperature with stirring, and stirred at the same temperature for 10 minutes. After ceasing the generation of hydrogen gas, 0.30 g of methyl iodide was added, and continued to stir further for 45 minutes. After the completion of the reaction, the reaction mixture was poured in 20 mL of ice water, extracted with ethyl acetate (50 mL×1), the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:2) to obtain 0.18 g of the aimed product as colorless resinous substance.

後処理

  1. stirringstirred at the same temperature for 10 minutes
  2. additionwas added
  3. stirringto stir further for 45 minutes
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (50 mL×1)
  6. dry with materialdried over saturated sodium chloride aqueous solution
  7. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

出典と根拠

ORDレコード
ord-d5709743909542ebb621d05870777213
出典データセット
uspto-grants-2011_05
特許番号
US07951828B1

反応ノート

読み込み中…