Cesium carbonate → 1-(cyclopropylmethyl)-4-iodo-1H-pyrazole

HRID 1466932Notes

Reaction equation

HRID 1466932 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Br[CH2:8][CH:9]1[CH2:11][CH2:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:9]1([CH2:8][N:4]2[CH:3]=[C:2]([I:1])[CH:6]=[N:5]2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 770224-IodopyrazoleHCID 81503Bromomethylcyclopropane

Product 1

HCID 644309831-(cyclopropylmethyl)-4-iodo-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Iodo-1H-pyrazole (0.50 g, 2.5 mmol), bromomethyl cyclopropane (0.75 mL, 7.5 mmol), and cesium carbonate (1.20 g, 3.75 mmol) were combined in DMF (10 mL) and stirred at room temperature for overnight. The mixture was subjected to standard aqueous workup, and the crude residue was purified on silica gel (0-20% EtOAc in hexanes) to afford the title compound.

Workup

  1. customthe crude residue was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b36178626e54437bb3bdb52c3f2f8f65
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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