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

HRID 1943889노트

반응식

HRID 1943889 반응식
[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

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178490916HCID 178490916, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-548c7dd7069f4ef68615f745575c500f
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394795B2

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