Cesium carbonate → N-(1-(4-Methoxyphenylsulfonyl)-2,3-dihydro-1H-indol-7-yl)isonicotinamide

HRID 18699

반응식

HRID 18699 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[NH2:21])[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[NH:21][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH2:14][CH2:13]2)(=[O:10])=[O:11])=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 247482541-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-ylamine

생성물 1

HCID 16215971N-(1-(4-Methoxyphenylsulfonyl)-2,3-dihydro-1H-indol-7-yl)isonicotinamide수율 82%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred mixture of 19 (0.2 g, 0.52 mmol), isonicotinoyl chloride hydrochloride (0.18 g, 1.04 mmol), and cesium carbonate (0.68 g, 2.08 mmol) in acetonitrile (20 ml) was heated to reflux for 16 h. The reaction mixture was quenched with ice water and extracted with CH2Cl2. The combined organic layer was dried over MgSO4 and evaporated to give a residue that was purified by silica gel flash column chromatography (EtOAc:n-hexane :NH3(aq)=3:2:1%) and recrystallized (CH2Cl2/EtOAc) to afford compound 26, yield 82%.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. customThe reaction mixture was quenched with ice water
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. customevaporated
  7. customto give a residue that
  8. customwas purified by silica gel flash column chromatography (EtOAc:n-hexane :NH3(aq)=3:2:1%)
  9. customrecrystallized (CH2Cl2/EtOAc)

출처 및 근거

ORD 기록
ord-9cabd8ab2a684028b3e6a1d2de242f8c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741495B2

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