HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloride → Methyl 2-(4-((2-(3-chlorophenyl)-6-(trifluoromethyl)pyridin-4-yl)methyl)phenyl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloride | HCID 312 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(2-Methoxy-2-oxoethyl)benzylboronic Acid Pinacol Ester | HCID 67494481 | — |
| Reactant | 4-Chloro-2-(3-chlorophenyl)-6-(trifluoromethyl)pyridine | HCID 90112657 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Methyl 2-(4-((2-(3-chlorophenyl)-6-(trifluoromethyl)pyridin-4-yl)methyl)phenyl)acetate | HCID 90111620 | — |
Reaction Steps
A 20-mL sealed tube, with stirrer bar, was charged with 4-chloro-2-(3-chlorophenyl)-6-(trifluoromethyl)pyridine (0.263 g, 0.90 mol), methyl 2-(4-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)phenyl)acetate (0.261 g, 0.90 mmol), Pd(dppf)Cl2 (0.073 g, 0.09 mmol), and powdered Na2CO3 (0.286 g, 2.70 mmol). Dioxane (8 mL) and water (4 mL) were added. The resulting mixture was stirred under Ar at 90° C. for 27 h. until the starting chloride was consumed. After cooling to room temperature, the reaction mixture was absorbed onto silica and purified by chromatography on silica using dichloromethane/methanol (10:0 to 9:1) as eluent to afford methyl 2-(4-((2-(3-chlorophenyl)-6-(trifluoromethyl)pyridin-4-yl)methyl)phenyl)acetate
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221843B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-32d194d14b3848b9910e1e4e95718dd9 |
| Source note | uspto-grants-2015_12 |