Water → 2-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275093노트

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HRID 2275093 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18](=[O:19])[C:17]3[C:16]4[C:11](=[CH:12][C:13]([C:20]#[N:21])=[CH:14][CH:15]=4)[NH:10][C:9]=3[C:8]([CH3:23])([CH3:22])[C:7]=2[CH:24]=1.C1C(=O)N([Br:32])C(=O)C1.O>CC#N>[Br:32][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[C:20]#[N:21])[NH:10][C:9]1[C:8]([CH3:22])([CH3:23])[C:7]3[CH:24]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[C:18](=[O:19])[C:17]2=1

참가 물질

5

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 668341058-Methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

생성물 1

HCID 668340982-Bromo-8-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

8-Methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A5-2, 50 mg, 0.158 mmol) was dissolved in CH3CN (1 mL), added with NBS (56 mg, 2 eq.), and stirred at 80° C. overnight. The reaction solution was added to water, and then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were added with MeOH and the solid remained after dissolution was filtered to obtain the target compound (yellow powder, 20 mg, 38%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. additionwere added with MeOH
  8. dissolutionafter dissolution
  9. filtrationwas filtered
  10. customto obtain the target compound (yellow powder, 20 mg, 38%)

출처 및 근거

ORD 기록
ord-e8527a97ef4844bfa7224824188a2283
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126931B2

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