Cesium carbonate → 4-Bromo-1-cyclopropyl-1H-pyrazole

HRID 515906Notes

Reaction equation

HRID 515906 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[CH:7]1(Br)[CH2:9][CH2:8]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:9][CH2:8]2)[CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 163754-BromopyrazoleHCID 78037Bromocyclopropane

Product 1

HCID 521420994-Bromo-1-cyclopropyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

4-Bromo-1H-pyrazole (1.76 g, 12 mmol) is dissolved in anhydrous dimethylformamide (15 mL). Cyclopropyl bromide (2.9 mL, 36 mmol) and caesium carbonate (7.8 g, 24 mmol) are successively added thereto. The reaction mixture is heated for 15 hours at 160° C. in a sealed flask. At the end of the reaction, the solvent is evaporated off in vacuo and the residue is purified by chromatography over silica gel using heptane and dichloromethane as eluants to yield the expected compound.

Workup

  1. customAt the end of the reaction
  2. customthe solvent is evaporated off in vacuo
  3. customthe residue is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-15dd0d8822634887b7bf93701d6c6f4b
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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