Water → HCID 67260594, compound

HRID 2359079Notes

Reaction equation

HRID 2359079 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)[S:5][C:6]=1[Br:7].[H-].[Na+].[CH:15](I)([CH3:17])[CH3:16].O>CN(C)C=O.CC(OC)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[CH:11][N:10]([CH:15]([CH3:17])[CH3:16])[N:9]=2)[S:5][C:6]=1[Br:7].[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH:15]([CH3:17])[CH3:16])[N:10]=[CH:11][CH:12]=2)[S:5][C:6]=1[Br:7]

Participants

8

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 178419313HCID 178419313, compound

Product 2

HCID 67260464HCID 67260464, compoundYield 7%HCID 67260594HCID 67260594, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

3-(4,5-dibromo-2-thienyl)-1H-pyrazole (9.4 mmol) was dissolved in 20 mL dry N,N-dimethylformamide under argon atmosphere. Sodium hydride (11.3 mmol, 60% dispersion in mineral oil) was added in portions at room temperature. The reaction mixture was stirred at room temperature for 15 min. Isopropyl iodide (14.1 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 14 h. Water and MTBE were added to the reaction mixture. The phases were separated and the aqueous phase was extracted with MTBE. The combined organic extracts were successively washed with water and brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (toluene:ethyl acetate 100:0 to 0:100) to afford 2.67 g 3-(4,5-dibromo-2-thienyl)-1-isopropyl-1H-pyrazole (81% yield) and 238 mg of 5-(4,5-dibromo-2-thienyl)-1-isopropyl-1H-pyrazole (7% yield).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 14 h
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with MTBE
  4. washThe combined organic extracts were successively washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (toluene:ethyl acetate 100:0 to 0:100)

Sources & evidence

ORD record
ord-9cbfe29a60d34327b26ca32db2feffba
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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