HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 45275574, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3,5-Dimethylisoxazole-4-boronic acid | HCID 2734346 | — |
| Reactant | HCID 45275354 | HCID 45275354 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 45275574 | HCID 45275574 | 17% |
Reaction Steps
General procedure E was followed using 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide E36 (100 mg, 0.35 mmol), 3,5-dimethyl-4-isoxazole boronic acid (74 mg, 0.53 mmol), tetrakis(triphenylphosphine)palladium(0) (20 mg, 5 mol %), acetonitrile (4 mL) and 0.5 M sodium carbonate (1.1 mL, 0.53 mmol). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 97:3-80:20, biotage 25+S) to furnish the title compound as a white solid (18 mg, 17%), along with 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide (10 mg, 10% RSM), LC-MS (ESI, 4 min) Rt 0.76 min, m/z 301 (100%, [M+H]+); m/z (ESI, Rt 1.22 min) C16H20N4O2 requires 300.1587, found [M+H]+ 300.1591.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08778925B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-9d1c373d88a44d3f987bc89403f69313 |
| Source note | uspto-grants-2014_07 |