HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Tert-butyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Chloro-2-formylphenylboronic acid | HCID 3806952 | — |
| Reactant | Tert-butyl 3-(5-bromopicolinamido)propanoate | HCID 71060050 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Tert-butyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate | HCID 86674275 | — |
Reaction Steps
tert-Butyl 3-(5-bromopicolinamido)propanoate (3.4 g, 10.3 mmol), (5-chloro-2-formylphenyl)boronic acid (2.1 g, 11.3 mmol), Pd(dppf)Cl2 (840 mg, 1.0 mmol), and K2CO3 (3.1 g, 22.6 mmol) were dissolved in 1,4-dioxane (35 mL) and water (9 mL) and heated to 90° C. After 3 h the resulting mixture was cooled to room temperature, diluted with EtOAc and water and the layers were separated. The combined organics were washed dried (Na2SO4), concentrated, 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-f9f8be8d853f46428403aa5ec5604dff |
| Source note | uspto-grants-2014_06 |