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Sodium hydride → 3-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one

HRID 2120228
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HRID 2120228 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[NH:14][C:15]([CH3:19])=[CH:16][C:17]=2[CH3:18])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29].N1CCCC1.[H-].[Na+]>N12CCCN=C1CCCCC2.CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[NH:14][C:15]([CH3:19])=[CH:16][C:17]=2[CH3:18])=[C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:20][C:21]2=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 321710OxindoleHCID 23439089(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone

생성물 1

HCID 539061583-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one수율 3.3%

시약·촉매·용매 3

HCID 81184
1,8-Diazabicyclo(5.4.0)undec-7-ene
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

(3,4-Dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone (100 mg, 0.4 mmol), oxindole (100 mg, 0.8 mmol), pyrrolidine (0.2 mL) and 1,8-diazabicyclo[5.4.0]undec-7-ene (a few drops) in dimethylforamide (1.5 mL) was heated at 160° C. for 2 hours. Sodium hydride (18 mg) was added to the reaction mixture and the heating was continued at 160° C. for 3 days. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was chromatographed eluting with ethyl acetate and hexane to give 5 mg of 3-[(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methylene]-1,3-dihydro-indol-2-one. MS EI 374 [M]+.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed
  6. washeluting with ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-7260a3583a434f72b910d5777a6ab168
출처 데이터셋
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06689806B1

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