Sodium hydride → HCID 86717531, compound

HRID 712071Notes

Reaction equation

HRID 712071 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][N:3]=1.[H-].[Na+].[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15]Cl>O1CCCC1.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:18])([CH3:17])[CH3:10])[N:3]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 12014233-Bromo-5-methyl-1H-pyrazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 86717531HCID 86717531, compoundYield 103%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromo-5-methyl-1H-pyrazole (from Ark Pharm, 6.4 g, 40 mmol) in tetrahydrofuran (263 mL) at 0° C. was added sodium hydride (3.2 g, 80 mmol). After stirring for 30 min, [β-(trimethylsilyl)ethoxy]methyl chloride (8.4 mL, 48 mmol) was added and the reaction mixture was allowed to warm to room temperature over 2 h. The reaction mixture was diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The crude was purified with flash chromatography (eluting with a gradient of 0-15% ethyl acetate in hexanes) to give the desired product as colorless oil (12 g, 100%). LCMS calculated for C10H20BrN2OSi (M+H)+: m/z=291.1. Found: 291.0.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified with flash chromatography (
  7. washeluting with a gradient of 0-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-88dac780d1034a3b95eb7ca81508d50a
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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