Sodium hydride → HCID 67078557, compound

HRID 1625995Notes

Reaction equation

HRID 1625995 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19].[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 404274545-Bromopyrazolo[3,4-b]pyridine

Product 1

HCID 67078557HCID 67078557, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-1H-pyrazolo[3,4-b]pyridine (200 mg) was dissolved in N,N-dimethylformamide (5 ml). 55% Sodium hydride (53 mg) was added at 0° C., and the mixture was stirred at the same temperature for five minutes and then stirred at room temperature for 20 minutes. 2-(Chloromethoxy)ethyltrimethylsilane (0.213 ml) was added and the mixture was stirred at 0° C. for 2 hours. A saturated aqueous ammonium chloride solution was added under ice-cooling, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (0.224 g).

Workup

  1. stirringstirred at room temperature for 20 minutes
  2. stirringthe mixture was stirred at 0° C. for 2 hours
  3. temperaturecooling
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b43a3d673e2c4793817a1932f2e57548
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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