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

HRID 21101ノート

反応式

HRID 21101 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
90 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-f23a68453a6c4b1fa08a3092beab187e
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

反応ノート

読み込み中…