Potassium Carbonate → 10-bromo-2-(3-carboxy-1-trans-propenyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850742노트

반응식

HRID 850742 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[C:17]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:16](=[O:26])[C:8]4[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34]/[CH:35]=[CH:36]/[C:37]([O:39]CC)=[O:38]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[C:17]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:16](=[O:26])[C:8]4[CH:9]=[C:10]([O:15]/[CH:34]=[CH:35]/[CH2:36][C:37]([OH:39])=[O:38])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5373944Ethyl (E)-4-bromobut-2-enoateHCID 1588691010-bromo-2-hydroxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

생성물 1

HCID 1588692410-bromo-2-(3-carboxy-1-trans-propenyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one수율 10%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

10-bromo-2-hydroxy-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (400 mg) obtained in Example 2 was suspended in dimethyl sulfoxide (30 ml), and to the suspension was added potassium carbonate (0.3 g), and the mixture was stirred at room temperature for 30 minutes. Ethyl 4-bromocrotonate (0.15 ml) was added and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice water (300 ml), and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: ethyl acetate). The resulting crude crystals were suspended in ethanol (20 ml), and 1N aqueous solution of sodium hydroxide (5 ml) was added to the suspension followed by stirring at room temperature for 12 hours. The solvent was evaporated under reduced pressure and the residue was extracted with water and ethyl acetate. 1N hydrochloric acid was added to the aqueous layer to a pH of 7, and the precipitated crystals were recovered by filtration to obtain the title compound (50 mg, 10%).

후처리

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel flash column chromatography (eluent: ethyl acetate)
  7. addition1N aqueous solution of sodium hydroxide (5 ml) was added to the suspension
  8. stirringby stirring at room temperature for 12 hours
  9. customThe solvent was evaporated under reduced pressure
  10. extractionthe residue was extracted with water and ethyl acetate
  11. addition1N hydrochloric acid was added to the aqueous layer to a pH of 7
  12. filtrationthe precipitated crystals were recovered by filtration

출처 및 근거

ORD 기록
ord-7c91dae632054bb39ae8c57bdbed994f
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06018046

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