Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 15340994 | HCID 15340994 | — |
| Catalyst | Copper | HCID 23978 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22316828 | HCID 22316828 | 16.2% |
Reaction Steps
To a suspention of sodium hydride (0.04 g: 1 mmol) (60% mineral oil dispersion; washed with dry hexane (3 mL)) in DMF(2 mL) was added imidazol (0.068 g) at room temperature and the mixture was stirred 30 minutes. Then, 4-[5-[4-Bromophenyl]-3-trifluoromethyl-1-[4-(methylsulfonyl)phenyl]-1H-pyrazole (0.445 g) and copper powder (0.0063 g) were added and the whole was heated at 150° C. for 3 hours. After cooling, water (30 mL) was added to the reaction mixture and the whole was extracted with CH2Cl2 (30 mL×2), the extract was washed with water and brine, dried over MgSO4,and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/methanol (1/0.03). The resulting solid was recrystallized with dichloroethane-diisopropyl ether to give the title compound (0.07 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06608095B2 |
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| Source dataset | uspto-grants-2003_08 |
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| ORD ID | ord-39b155c7c23841e39c24450b23147552 |
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| Source note | uspto-grants-2003_08 |
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