HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ethyl 3-(5-(3-chloro-5-formylphenyl)picolinamido)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Bromo-5-chlorobenzaldehyde | HCID 17750952 | — |
| Reactant | Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate | HCID 71059832 | — |
| 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-(3-chloro-5-formylphenyl)picolinamido)propanoate | HCID 86674297 | — |
Reaction Steps
3-bromo-5-chlorobenzaldehyde (502 mg, 2.3 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (794 mg, 2.3 mmol), Pd(dppf)Cl2 (84 mg, 0.1 mmol), and K2CO3 (632 mg, 4.6 mmol) were dissolved in 1,4-dioxane (10 mL) and water (2 mL) and the resulting mixture was heated to 70° C. After 3 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, 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-0ca8c18335c4400d857c89e8a1b0a75b |
| Source note | uspto-grants-2014_06 |