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

HRID 18699

反応式

HRID 18699 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-9cabd8ab2a684028b3e6a1d2de242f8c
出典データセット
uspto-grants-2010_06
特許番号
US07741495B2

関連ノート

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