Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Formylphenylboronic Acid | HCID 591073 | — |
| Reactant | [3-(3-Bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate | HCID 58276234 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Toluene ethanol | HCID 21863594 | — |
| Product | HCID 58276770 | HCID 58276770 | — |
Reaction Steps
A vial equipped with magnetic spin vane was charged with [[3-(3-Bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate (0.203 g; 0.60 mmol; Ex IV-24), 4-formylphenyl boronic acid (0.099 g; 0.66 mmol), and PdCl2(dppf).CH2Cl2 (0.012 g; 0.015 mmol), was sealed with a septum and evacuated/backfilled with N2 (×3). PhMe/EtOH (4:1, 3 mL) and 2M Na2CO3 (0.72 mL; 1.44 mmol) were added through the septum via syringe and the mixture was stirred at 80° C. for 2.5 h. Upon cooling, the mixture was partitioned between EtOAc/water and the layers were separated. The aqueous layer was extracted with EtOAc (×2), combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum/film. LC/MS (method A) 2.60 min; m/z 364 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08822518B2 |
|---|
| Source dataset | uspto-grants-2014_09 |
|---|
| ORD ID | ord-8f0c34c04c3246e0b91efc9283b60910 |
|---|
| Source note | uspto-grants-2014_09 |
|---|
