Water → 3-bromo-1-(2-methoxyethyl)-1H-pyrazole

HRID 1526302Notes

Reaction equation

HRID 1526302 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][N:4]([CH2:7][CH2:8][OH:9])[N:3]=1.[H-].[Na+].I[CH3:13].O>CN(C)C=O>[Br:1][C:2]1[CH:6]=[CH:5][N:4]([CH2:7][CH2:8][O:9][CH3:13])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 594022992-(3-bromo-1H-pyrazol-1-yl)ethan-1-ol

Product 1

HCID 971789773-bromo-1-(2-methoxyethyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-bromo-1H-pyrazol-1-yl)ethanol obtained in Step D of Example 6 (300 mg) in N,N-dimethylformamide (16 mL) were added sodium hydride (55%, 137 mg) and iodomethane (196 μL) under ice-cooling. The reaction mixture was stirred under ice-cooling for 2 hr, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (150 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-71e9632191554930a2cd0d0635f241e0
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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