Water → 6-Fluoro-3-(4-{[3-(2-methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]oxy}phenyl)-1-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 573367ノート

反応式

HRID 573367 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[N:10]([CH3:11])[N:9]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:21][O:22][CH2:23][CH2:24][N:25]1[C:29]2=[N:30][CH:31]=[CH:32][CH:33]=[C:28]2[N:27]=[C:26]1S(C)(=O)=O.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[N:10]([CH3:11])[N:9]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:26]4[N:25]([CH2:24][CH2:23][O:22][CH3:21])[C:29]5=[N:30][CH:31]=[CH:32][CH:33]=[C:28]5[N:27]=4)=[CH:14][CH:13]=3)[C:5]2=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 667277733-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 1364090944-(6-Fluoro-1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol

生成物 1

HCID 667280596-Fluoro-3-(4-{[3-(2-methoxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]oxy}phenyl)-1-methyl-1H-pyrazolo[4,3-b]pyridine収率 44%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 4-(6-fluoro-1-methyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenol (37 mg) in DMF (4 mL) was added NaH (60% in oil, 4.02 mg) at room temperature. The mixture was stirred at room temperature for 30 min, and then 3-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (52 mg) was added. The mixture was exposed to microwave irradiation at 180° C. for 30 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane). The product was crystallized from EtOH/hexane to give the title compound (28.0 mg).

後処理

  1. customirradiation at 180° C. for 30 min
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane)
  6. customThe product was crystallized from EtOH/hexane

出典と根拠

ORDレコード
ord-bb6df8bde08f4748b6c734ef47395d13
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

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