4-Aminophenol → HCID 59373928、化合物

HRID 473693

反応式

HRID 473693 の反応式
F[C:2]1[C:7]([C:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1>CS(C)=O.CCOC(C)=O>[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:2]2[C:7]([C:8]3[CH2:13][CH2:12][N:11]([C:14](=[O:16])[CH3:15])[CH2:10][CH:9]=3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:26][CH:25]=1

参加物

6

反応物 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 593269651-(4-(2-fluoropyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

生成物 1

HCID 59373928HCID 59373928、化合物

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A solution of 1-(4-(2-fluoropyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (1.68 g, 7.63 mmol) in dimethylsulfoxide (25 mL) under argon was added cesium carbonate (2.73 g, 8.39 mmol), followed by 4-aminophenol (0.874 g, 8.01 mmol). The reaction was stirred at 80° C. for 18 h. The cooled reaction mixture was diluted with EtOAc and washed with water; the aqueous layer was back-extracted with EtOAc (1×). The organic layers were combined, dried (MgSO4), filtered, and concentrated in vacuo. Flash column chromatography (20% to 50% EtOAc/Hexanes) afforded 1-(4-(2-(4-aminophenoxy)-pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone as a tan solid. MS (ESI, pos. ion) m/z: 310.0 (M+1).

後処理

  1. customThe cooled reaction mixture
  2. washwashed with water
  3. extractionthe aqueous layer was back-extracted with EtOAc (1×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0159fd29973e417aa6442dc223c8c2de
出典データセット
uspto-grants-2014_01
特許番号
US08637500B2

関連ノート

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