Water → 4-(3-bromo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl oxy)-butyric acid methyl ester

HRID 61808

반응식

HRID 61808 반응식
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7](=[O:22])[C:8]4[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:9]=4[C:10]([CH3:16])([CH3:15])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[CH3:23][O:24][C:25](=[O:30])[CH2:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(N(C)C)=O>[CH3:23][O:24][C:25](=[O:30])[CH2:26][CH2:27][CH2:28][O:21][C:19]1[CH:18]=[CH:17][C:9]2[C:10]([CH3:16])([CH3:15])[C:11]3[NH:12][C:13]4[C:5]([C:6]=3[C:7](=[O:22])[C:8]=2[CH:20]=1)=[CH:4][CH:3]=[C:2]([Br:1])[CH:14]=4

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 107604Methyl 4-bromobutyrate2회HCID 668347143-Bromo-9-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

생성물 1

HCID 668342214-(3-bromo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl oxy)-butyric acid methyl ester

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

3-Bromo-9-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound JJ2, 20 mg, 0.056 mmol), 4-bromo-butyric acid methyl ester (7.0 μl, 0.056 mmol) and cesium carbonate (36.6 mg, 0.112 mmol) were dissolved in DMA (0.09 ml), and then stirred at room temperature for 1 hr. Thereafter, 4-bromo-butyric acid methyl ester (7.0 μl, 0.056 mmol) was added thereto and the mixture was stirred at room temperature for 3 hr, followed by further stirring at 45° C. for 30 min. The reaction solution was added with water, extracted with diethyl ether and dried over anhydrous magnesium sulfate. After the concentration under reduced pressure, the resulting residues were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain 4-(3-bromo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-9-yl oxy)-butyric acid methyl ester. This compound was dissolved in MeOH (0.50 ml), added with aqueous solution of sodium hydroxide (6 mol/1), and then stirred at room temperature for 10 min. The reaction solution was added with hydrochloric acid (3 mol/1), extracted with diethyl ether, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain white solid. This white solid was washed with methylene chloride to obtain the title compound (6.1 mg, 25%).

후처리

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. stirringby further stirring at 45° C. for 30 min
  3. extractionextracted with diethyl ether
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter the concentration under reduced pressure
  6. customthe resulting residues were purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-c164e1ad47654720995ab3935bae4666
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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