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

HRID 573361ノート

反応式

HRID 573361 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][N:22]1[C:26]2=[N:27][CH:28]=[CH:29][CH:30]=[C:25]2[N:24]=[C:23]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:23]4[N:22]([CH3:21])[C:26]5=[N:27][CH:28]=[CH:29][CH:30]=[C:25]5[N:24]=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 585773713-Methyl-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 566520666-Fluoro-1-methyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[4,3-b]pyridine収率 43.4%

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 (120 mg) in DMF (4 mL) was added NaH (60% in oil, 11.84 mg) at room temperature. The mixture was stirred at room temperature for 30 min, and then 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (104 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 (80 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-132f64e63450448096738afd813c68d3
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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