Methyl iodide → 2-(2-Methyl-5-phenyl-pyrazol-3-yl)isoindoline-1,3-dione

HRID 2205841ノート

反応式

HRID 2205841 の反応式
[H-].[Na+].[C:3]1([C:9]2[CH:13]=[C:12]([N:14]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:24])[NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:25]I>CN(C=O)C.O>[CH3:25][N:11]1[C:12]([N:14]2[C:15](=[O:24])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]2=[O:23])=[CH:13][C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[N:10]1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178514955HCID 178514955、化合物

生成物 1

HCID 867173302-(2-Methyl-5-phenyl-pyrazol-3-yl)isoindoline-1,3-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (830 mg, 0.02 mol) was added portionwise to a mixture of 2-(3-phenyl-1H-pyrazol-5-yl)isoindoline-1,3-dione (5 g, 0.0173 mol) and methyl iodide (1.5 mL, 0.024 mol) in DMF (80 mL) at 10° C. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water and the aqueous phase was extracted with ethyl acetate twice. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:19 to 2:8) yielding a mixture of the title compound and the regioisomer 2-(2-methyl-5-phenyl-pyrazol-3-yl)isoindoline-1,3-dione (850 mg, 5:1).

後処理

  1. extractionthe aqueous phase was extracted with ethyl acetate twice
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:19 to 2:8)
  6. customyielding

出典と根拠

ORDレコード
ord-7bff7eedcfa246b8a3890ff0a9c15aa1
出典データセット
uspto-grants-2016_06
特許番号
US09371332B2

反応ノート

読み込み中…