Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4-[(4-Bromophenyl)methyl]-5-cyclohexyl-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole | HCID 67334736 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | HCID 67335137 | HCID 67335137 | — |
Reaction Steps
A mixture of 782 mg 4-(4-bromobenzyl)-5-cyclohexyl-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole from Step D above, 115 mg zinc cyanide, and 94 mg tetrakis(triphenylphosphine)palladium(0) in 5 mL DMF was heated under nitrogen in a 75° C. oil bath over night. Evaporate most of DMF. The residue was purified on silica gel using 10-40% EtOAc in hexanes to give the title compound as a yellowish solid. 1H NMR (CDCl3, 500 MHz) δ 7.61˜7.64 (m, 2H), 7.40˜7.44 (m, 2H), 7.33˜7.37 (m, 4), 7.31 (s, 1H), 4.06 (s, 2H), 2.70 (tt, J=3.1 & 12.5 Hz, 1H), 1.73˜1.79 (m, 4H), 1.66˜1.71 (m, 1H), 1.50˜1.58 (m, 2H), 1.09˜1.24 (m, 3H). LC-MS: 2.46 min. (M+H=426.2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07572922B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-b7c5ce32c29f47359e30e3fdd583de49 |
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| Source note | uspto-grants-2009_08 |
|---|