HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-[3,5-bis(trifluoromethyl)phenyl]-N-(6'-chloro-6-fluoro-2-methyl-3,4'-bipyridin-3'-yl)-N,2-dimethylpropanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Fluoro-6-methylpiperidine-5 boronic acid | HCID 66658552 | — |
| Reactant | 2-[3,5-bis(trifluoromethyl)phenyl]-N-(6-chloro-4-iodo-3-pyridinyl)-N,2-dimethylpropanamide | HCID 86624198 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-[3,5-bis(trifluoromethyl)phenyl]-N-(6'-chloro-6-fluoro-2-methyl-3,4'-bipyridin-3'-yl)-N,2-dimethylpropanamide | HCID 59215822 | — |
Reaction Steps
2-[3,5-bis(trifluoromethyl)phenyl]-N-(6-chloro-4-iodo-3-pyridinyl)-N,2-dimethylpropanamide (200 mg, 0.363 mmol), 2-fluoro-6-methylpiperidine-5 boronic acid (73 mg, 0.472 mmol), sodium carbonate solution (0.4 mL, 2M), tetrakistriphenylphosphinepalladium (4 mg, 0.00363 mmol) in dioxan (2 mL) were heated together in the microwave at 110° C. for 30 minutes. The mixture was partitioned between EtOAc and sat NaHCO3 solution. Aqueous layer extracted with EtOAc×3. Combined extracts dried and evaporated. Residue purified on a 12+M horizon column eluting with Pet Et2O to 60% EtOAc/Pet Et2O, Solvent evaporated under reduced pressure to afford the title compound in quantitative yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08097618B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-6560d879df9c4ff6975f974abe0faee9 |
| Source note | uspto-grants-2012_01 |