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Chlorosuccinimide → HCID 178471819, 화합물

HRID 2378920
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HRID 2378920 반응식
[C:1]([O:4][CH2:5][C:6]1[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][C:12]([Br:28])=[C:11]2[C:7]=1[CH:8]=[N:9][NH:10]2)(=[O:3])[CH3:2].[Cl:29]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[C:14]([CH2:15][C@@H:16]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][C:12]([Br:28])=[C:11]2[C:7]=1[C:8]([Cl:29])=[N:9][NH:10]2)(=[O:3])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 31398ChlorosuccinimideHCID 59731854(S)-Diethyl 2-((4-(acetoxymethyl)-7-bromo-1H-indazol-5-yl)methyl)succinate

생성물 1

HCID 178471819HCID 178471819, 화합물수율 88%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

(S)-Diethyl 2-((4-(acetoxymethyl)-7-bromo-1H-indazol-5-yl)methyl)succinate(400 mg, 0.879 mmol) was dissolved in N,N-dimethylformamide (5.0 ml). N-Chlorosuccinimide (130 mg, 0.974 mmol) was added to the solution. Mixture was warmed to 150° C. and held with stirring for 1.5 hours. Mixture was cooled to room temperature and then diluted with ethyl acetate. Material was washed twice with water and the aqueous phase was discarded. Material was washed with brine and the aqueous phase was discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Silica gel chromatography eluting ethyl acetate-hexanes afforded the title compound as clear colorless oil in 88% yield. MS (M+H)+=491.0.

후처리

  1. temperatureMixture was cooled to room temperature
  2. washMaterial was washed twice with water
  3. washMaterial was washed with brine
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. washSilica gel chromatography eluting ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-3480f8b6433f46f9943a70969f088366
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07470680B2

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