3-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one → 3-[5-(3-dimethylamino-propyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one

HRID 1829049

반응식

HRID 1829049 반응식
[CH3:1][N:2]([CH3:25])[CH2:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[C:15]1[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]1=[O:24])[O:10][CH2:9]2.[H][H]>[Pd].CO>[CH3:25][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[C:15]1[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]1=[O:24])[O:10][CH2:9]2

참가 물질

5

반응물 2

HCID 696591513-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-oneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 696594463-[5-(3-dimethylamino-propyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one수율 23%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of 3-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one (300 mg, 0.91 mmol) and 10% palladium on carbon (60 mg) in MeOH (20 ml) was shaken under 43 psi of hydrogen for 4 hours. The catalyst was removed by filtration through celite and rinsed with MeOH. The combined filtrates were evaporated to give a crude product. The crude product was purified by silica gel column chromatography, eluted with a gradient of MeOH in CHCl3, to give 3-[5-(3-dimethylamino-propyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a yellow solid (70 mg, 23%).

후처리

  1. customThe catalyst was removed by filtration through celite
  2. washrinsed with MeOH
  3. customThe combined filtrates were evaporated
  4. customto give a crude product
  5. customThe crude product was purified by silica gel column chromatography
  6. washeluted with a gradient of MeOH in CHCl3

출처 및 근거

ORD 기록
ord-5bdbd0a04c5143319003b81deff61efc
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060844B2

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