m-Chloroperbenzoic acid → 4-oxido-4-(2-{[1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yl]oxy}ethyl)morpholin-4-ium

HRID 331291노트

반응식

HRID 331291 반응식
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[C:15]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:40])C=1>C(Cl)Cl.CCOC(C)=O>[O-:40][N+:4]1([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[C:15]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

참가 물질

5

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 509405096-(2-morpholinoethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one

생성물 1

HCID 866698614-oxido-4-(2-{[1-oxo-3-phenyl-2-(pyridin-3-yl)-1H-inden-6-yl]oxy}ethyl)morpholin-4-ium수율 26.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-(2-morpholinoethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one (100 mg, 0.24 mmol) obtained in Step 7 of Example 1 in CH2Cl2 (2 mL) at 10° C. was added MCPBA (21 mg, 1 eq). The mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc and washed with sat. NaHCO3, H2O, and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (MC/MeOH/NH4OH=92:7:1) to afford the title compound (14 mg, 13%).

후처리

  1. washwashed with sat. NaHCO3, H2O, and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (MC/MeOH/NH4OH=92:7:1)

출처 및 근거

ORD 기록
ord-0f59250d38bf4a6981760ae83744cea1
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877747B2

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