Water → 7-Amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone

HRID 21101노트

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HRID 21101 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](Br)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[C:13](=[O:16])([O-])[O-].[K+].[K+].[OH2:19]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:2]2[CH:3]=[CH:4][C:5]([OH:19])=[C:6]([O:16][CH3:13])[CH:10]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

참가 물질

4

반응물 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 197019327-Amino-4-bromo-2,3-dihydroisoindol-1-one

생성물 1

HCID 684876617-Amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone수율 94%

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온도
90 °C

실험 절차

7-Amino-4-bromoisoindolinone (150 mg, 0.661 mmol) was dissolved in dimethoxythane (10.5 mL), and the solution was added with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenol (331 mg, 1.32 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (43.2 mg, 0.0529 mmol) and potassium carbonate (456 mg, 3.31 mmol), and stirred at 90° C. for 4.3 hours under argon atmosphere. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=4/1, chloroform/methanol=10/1) to obtain 7-amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone (169 mg, yield 94%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=4/1, chloroform/methanol=10/1)

출처 및 근거

ORD 기록
ord-f23a68453a6c4b1fa08a3092beab187e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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