Water → HCID 67034657, compound

HRID 539122Notes

Reaction equation

HRID 539122 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[CH:11][N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178419346HCID 178419346, compound

Product 1

HCID 67034657HCID 67034657, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-(4-bromophenyl)-1H-pyrazole (2.0 g, 9.0 mmol) in DMF was added sodium hydride (0.54 g, 13 mmol) (60% in oil) and the reaction was stirred at ambient temperature for 30 minutes. (2-(Chloromethoxy)ethyl)trimethylsilane (4.5 g, 27 mmol) was added and the reaction was stirred overnight. Water was added and the aqueous phase extracted with DCM. The combined organic phases were dried over MgSO4, filtered and concentrated. The crude material was purified by reverse phase chromatography (SP4, 25M, water/CH3CN 60:40 to 0:100, 20 column volumes) to yield 3-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (2.4 g, 76% yield) as a clear oil.

Workup

  1. stirringthe reaction was stirred overnight
  2. extractionthe aqueous phase extracted with DCM
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by reverse phase chromatography (SP4, 25M, water/CH3CN 60:40 to 0:100, 20 column volumes)

Sources & evidence

ORD record
ord-3c5685a2ca92414787715bb021929e92
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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