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

HRID 573315ノート

反応式

HRID 573315 の反応式
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[CH:10][N:11]=[C:6]2[C:5]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[N:4]1)[CH3:2].[CH3:19][N:20]1[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:23]2[N:22]=[C:21]1S(C)(=O)=O.[H-].[Na+].O>CN(C=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[CH:10][N:11]=[C:6]2[C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:21]3[N:20]([CH3:19])[C:24]4=[N:25][CH:26]=[CH:27][CH:28]=[C:23]4[N:22]=3)=[CH:14][CH:13]=2)=[N:4]1)[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridineHCID 1363976954-(1-Ethyl-1H-pyrazolo[3,4-b]pyrazin-3-yl)phenol

生成物 1

HCID 667279281-Ethyl-3-{4-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)oxy]phenyl}-1H-pyrazolo[3,4-b]pyrazine収率 63.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

To a solution of 4-(1-ethyl-1H-pyrazolo[3,4-b]pyrazin-3-yl)phenol (100 mg) and 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (88 mg) in DMF (3 mL) was added NaH (60% in oil, 17 mg) at room temperature, and the mixture was heated at 150° C. for 1.5 h under microwave irradiation. The mixture was poured into water and extracted with AcOEt. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane) and recrystallized from AcOEt/hexane to give the title compound (98 mg).

後処理

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane)
  6. customrecrystallized from AcOEt/hexane

出典と根拠

ORDレコード
ord-f361fe5f34ae4441b3824e4f26c64e6b
出典データセット
uspto-grants-2015_05
特許番号
US09029536B2

反応ノート

読み込み中…