Sodium hydride → 1-Cyclopropyl-4-iodo-1H-pyrazole
Reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].Br[CH:10]1[CH2:12][CH2:11]1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:10]1([N:4]2[CH:3]=[C:2]([I:1])[CH:6]=[N:5]2)[CH2:12][CH2:11]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 140 °C
Procedure
To a stirred solution of 4-Iodo-1H-pyrazole (2.0 g, 10.3 mmol) in DMF (100 mL) at room temperature was added sodium hydride (0.45 g of a 60% wt/wt dispersion in mineral oil, 11.3 mmol). After 15 minutes, bromocyclopropane (2.5 mL, 30.9 mmol), and tetra-n-butyl ammonium iodide (0.020 g) were added, and the reaction mixture was warmed to 140° C. 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
- customthe crude residue was purified on silica gel (0-20% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-c4d8e1f9bb814378944f09c370f382b0
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09000025B2
Reaction notes
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