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

HRID 61717ノート

反応式

HRID 61717 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-d089bde9a01e42148730473b844ecee9
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

反応ノート

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