1-Bromo-2-methylpropane → HCID 67260785, compound

HRID 2359067Notes

Reaction equation

HRID 2359067 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:11]=[CH:10][NH:9][N:8]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][CH:20]([CH3:22])[CH3:21]>CN(C)C=O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:11]=[CH:10][N:9]([CH2:19][CH:20]([CH3:22])[CH3:21])[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 10796Cesium carbonateHCID 178477947HCID 178477947, compound

Product 1

HCID 67260785HCID 67260785, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-chloro-2-thienyl)-1H-pyrazole (1 eq, 0.023 mol) and cesium carbonate (1.2 eq, 0.028 mol) in dry N,N-dimethylformamide (50 mL) was added 1-bromo-2-methylpropane (1.1 eq, 0.025 mol) slowly and the mixture was stirred at room temperature for 3 h. After completion of the reaction monitored by TLC, the reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude compound was purified by column-chromatography to afford 4.3 g of 3-(5-chloro-2-thienyl)-1-isobutyl-1H-pyrazole (76% yield).

Workup

  1. additionthe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude compound was purified by column-chromatography

Sources & evidence

ORD record
ord-751bacc05c6c476590d150ba7ed24434
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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