HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ethyl 3-(5-(2-(((2',4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate | HCID 71059832 | — |
| Reactant | N-(2-bromo-4-(trifluoromethyl)benzyl)-2',4'-dichloro-[1,1'-biphenyl]-4-amine | HCID 86674248 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Ethyl 3-(5-(2-(((2',4'-dichloro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate | HCID 71060009 | — |
Reaction Steps
N-(2-bromo-4-(trifluoromethyl)benzyl)-2′,4′-dichloro-[1,1′-biphenyl]-4-amine (386 mg, 0.8 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate, prepared as in step a, (424 mg, 1.2 mmol), Pd(dppf)Cl2 (67 mg, 0.1 mmol), and K2CO3 (225 mg, 1.6 mmol) were dissolved in 1,4-dioxane (8 mL) and water (2 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08748624B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-05d027eacce74e70839d2ea5be5f8ec1 |
| Source note | uspto-grants-2014_06 |