4-Bromopyrazole → 4-BroMo-1-cyclobutylpyrazole

HRID 2176529Notes

Reaction equation

HRID 2176529 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].Br[CH:10]1[CH2:13][CH2:12][CH2:11]1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:10]2[CH2:13][CH2:12][CH2:11]2)[CH:6]=1

Participants

6

Reactant 3

HCID 163754-BromopyrazoleHCID 24758Sodium hydrideHCID 78110Bromocyclobutane

Product 1

HCID 665214554-BroMo-1-cyclobutylpyrazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0 C) stirred solution of 4-bromo-1H-pyrazole (5.360 g, 36.47 mmol) in DMF (50 mL) was added sodium hydride (1.925 g, 80.23 mmol) slowly. The mixture was allowed to stir in the ice bath 30 min and bromocyclobutane (3.433 ml, 36.47 mmol) was added. The vessel was sealed and the reaction mixture heated at 95 C for 23 h. The mixture was allowed to cool to rt and diluted with 200 mL EtOAc, washed with 500 mL water, then 2×100 mL water, sat NaHCO3, then the organic layer dried over Na2SO4, filtered and evaporated. The mixture was purified via flash chromatography using a CH2Cl2 in hexanes gradient. (I2 stain for visualization). The title compound was collected as a colorless liquid.

Workup

  1. temperatureTo a cooled (0 C)
  2. additionwas added
  3. customThe vessel was sealed
  4. temperaturethe reaction mixture heated at 95 C for 23 h
  5. washwashed with 500 mL water
  6. dry with materialthe organic layer dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe mixture was purified via flash chromatography
  10. customThe title compound was collected as a colorless liquid

Sources & evidence

ORD record
ord-e61a33e4c3c2477d942c53ffae5a51b7
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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