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

HRID 1943889Notes

Reaction equation

HRID 1943889 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-548c7dd7069f4ef68615f745575c500f
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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