HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → (S)-tert-Butyl 4-(4-bromo-1H-pyrazol-1-yl)-1-(4-chlorophenyl)butan-2-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromopyrazole | HCID 16375 | — |
| Reactant | (S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate | HCID 57950570 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-tert-Butyl 4-(4-bromo-1H-pyrazol-1-yl)-1-(4-chlorophenyl)butan-2-ylcarbamate | HCID 57950651 | 93.3% |
Reaction Steps
To a mixture of 4-bromopyrazole (1.26 g, 8.57 mmol) and cesium carbonate (4.66 g, 14.3 mmol) in DMF (20 mL) was added (3S)-3-((tert-butoxycarbonyl)amino)-4-(4-chlorophenyl)butyl methanesulfonate (2.70 g, 7.15 mmol). The mixture was stirred for 16 hours at room temperature. The mixture was diluted with DCM and washed with H2O (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (EtOAc/Hexanes, 0-25%) to give the product as an off-white solid (2.86 g, 93%). LCMS (API-ES) m/z: 428, 430 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07897619B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-e76123ddf8244b0cbab98712674a6100 |
| Source note | uspto-grants-2011_03 |