HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Methyl 2'-cyano-5-(5-methylpyridin-2-yl)-5'-(trifluoromethyl)biphenyl-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromo-4-(trifluoromethyl)benzonitrile | HCID 3015802 | — |
| Reactant | Methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate | HCID 59432564 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 2'-cyano-5-(5-methylpyridin-2-yl)-5'-(trifluoromethyl)biphenyl-3-carboxylate | HCID 58449399 | — |
Reaction Steps
Into a 5 mL microwave vial were charged methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (300 mg, 0.85 mmol), 2-bromo-4-(trifluoromethyl)benzonitrile (425 mg, 1.70 mmol), cesium carbonate (1.38 g, 4.25 mmol), tetra-n-butylammonium iodide (314 mg, 0.85 mmol), POPd (43 mg, 0.085 mmol), water (0.6 mL) and N,N-dimethylformamide (3 mL). The reaction mixture was subjected to microwave irradiation at 150° C. for 10 mins. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to afford the residue which was purified by silica gel column to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133122B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-088f1dc84df64f43ac47bef8e5d1a8dc |
| Source note | uspto-grants-2015_09 |