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

HRID 2205841노트

반응식

HRID 2205841 반응식
[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

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178514955HCID 178514955, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7bff7eedcfa246b8a3890ff0a9c15aa1
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371332B2

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