Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Tert-butyl 4-iodopiperidine-1-carboxylate | HCID 10892302 | — |
| Reactant | HCID 178468958 | HCID 178468958 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59843183 | HCID 59843183 | 39.9% |
Reaction Steps
tert-Butyl 4-iodopiperidine-1-carboxylate (5.683, 18.26 mmol, E.G. Corley et al, JOC, 2004, 69, 5120-5123) in DMF (30.7 ml) was added to a mixture of ethyl 3-(trifluoromethyl)-1H-pyrazole-5-carboxylate (3.2 g, 15.37 mmol, M.-A. Plancquaert et al, Tetrahedron, 52, 4383-4396) and potassium carbonate 95.31 g, 38.4 mmol) and the mixture was stirred at 80° C. for 16 h. After cooling, water was added and the mixture was extracted with EtOAc, and the organic extraxts were dried, filtered and concentrated. Chromatographic purification of the residue by Biotage (5-20% EtOAc in Hexanes, 25M column) gave compound 93 as colorless oil (2.4 g, 39.9% yield). LRMS (ESI): calc. 391.4; found 414.1 (M+Na)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08338437B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-93a7ca9a478d4fe792260820b42615ad |
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| Source note | uspto-grants-2012_12 |
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