Potassium Carbonate → 10-bromo-2-(2-oxopentyloxy)-4H-pyrido [3,2,1-jk]carbazole-4-one

HRID 850772노트

반응식

HRID 850772 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[CH:17][C:16](=[O:19])[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[CH2:27][C:28](=[O:32])[CH2:29][CH2:30][CH3:31]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:18]=[CH:17][C:16](=[O:19])[C:8]4[CH:9]=[C:10]([O:15][CH2:27][C:28](=[O:32])[CH2:29][CH2:30][CH3:31])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 100578691-Bromopentan-2-oneHCID 2125288410-bromo-2-hydroxy-4H-pyrido[3,2,1-jk]carbazole-4-one

생성물 1

HCID 1936487310-bromo-2-(2-oxopentyloxy)-4H-pyrido [3,2,1-jk]carbazole-4-one수율 41%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

10-bromo-2-hydroxy-4H-pyrido3,2,1-jk]carbazole-4-one (250 mg) obtained in Example 59 was suspended in dimethyl sulfoxide (10 ml), and potassium carbonate (210 mg) was added to the suspension. The mixture was stirred at room temperature for 30 minutes and 1-bromo-2-pentanone (170 mg) was added to the mixture. The mixture was stirred at room temperature for 3 hours, and the reaction mixture was poured into ice water 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: methylene chloride containing 2% methanol) to obtain the title compound (130 mg, 41%).

후처리

  1. stirringThe mixture was stirred at room temperature for 3 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: methylene chloride containing 2% methanol)

출처 및 근거

ORD 기록
ord-3c945a4dc9f54367b2aca50167157949
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06018046

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