HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Tert-butyl 3-(5-(5-chloro-2-(((3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride) | HCID 2734385 | — |
| Reactant | Tert-butyl 3-(5-(2-(((4-bromophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate | HCID 71059988 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Tert-butyl 3-(5-(5-chloro-2-(((3'-(trifluoromethoxy)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate | HCID 71060116 | — |
Reaction Steps
tert-Butyl 3-(5-(5-chloro-2-(((4-bromophenyl)amino)methyl)phenyl)picolinamido)propanoate (82 mg, 0.15 mmol), (3-(trifluoromethoxy)phenyl)boronic acid (41 mg, 0.20 mmol), Pd(dppf)Cl2 (18 mg, 0.02 mmol), and K2CO3 (55 mg, 0.40 mmol) were dissolved in 1,4-dioxane (1.5 mL) and water (0.5 mL) and heated to 120° C. in the microwave. After 1 h the resulting mixture was diluted with DCM, dried (Na2SO4), filtered through CELITE, and purified via column chromatography to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08748624B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-f96f4fdae4324b858c9d4f83bd8f18ce |
| Source note | uspto-grants-2014_06 |