Potassium Carbonate → 4-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

HRID 2047197Notes

Reaction equation

HRID 2047197 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:18][O:17][CH2:16][CH2:15][Si:14]([CH3:21])([CH3:20])[CH3:13])[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 163754-BromopyrazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 156408714-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazoleYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100 mL roundbottom flask was charged 4-bromopyrazole (13.6 mmol, 2.00 g), K2CO3 (20.4 mmol, 2.82 g), and DMF (20 mL). To this suspension was added 2-(trimethylsilyl)ethoxymethyl chloride (15.0 mmol, 2.64 mL). This suspension was allowed to stir at room temperature 18 hours. The reaction mixture was then concentrated in vacuo, dissolved in 20 mL DCM, and filtered through celite. The crude mixture was purified via silica gel chromatography (0% to 80% ethyl acetate in hexanes gradient) to yield 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (2.53 g, 9.12 mmol, 67% yield) as clear oil.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutiondissolved in 20 mL DCM
  3. filtrationfiltered through celite
  4. customThe crude mixture was purified via silica gel chromatography (0% to 80% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-7a1fcaa0b7434441a22f30cb579d1d15
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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