Methyl iodide → 5-bromo-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1943889ノート

反応式

HRID 1943889 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([OH:11])=[N:9][N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([O:11][CH3:23])=[N:9][N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:5]2=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178490916HCID 178490916、化合物

生成物 1

HCID 670888295-bromo-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine収率 52.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-Bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-ol (0.200 g, 0.599 mmol) was dissolved in DMF. Sodium hydride (0.0287 g, 0.718 mmol) was added and stirred for 10 minutes. Methyl iodide (0.0448 mL, 0.718 mmol) was added, and the reaction mixture was stirred overnight. The solution was partitioned between water and EtOAc. The organic layer was washed with water (3×), brine, dried over Na2SO4 and concentrated to an oil, which was purified by column chromatography (2:1 hexanes/EtOAc) to give 5-bromo-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (0.11 g, 52.3%) as an oil.

後処理

  1. stirringthe reaction mixture was stirred overnight
  2. customThe solution was partitioned between water and EtOAc
  3. washThe organic layer was washed with water (3×), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil, which
  6. customwas purified by column chromatography (2:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-548c7dd7069f4ef68615f745575c500f
出典データセット
uspto-grants-2013_03
特許番号
US08394795B2

反応ノート

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