HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoro-methanesulfonic acid 4-methyl-6-(4-trifluoromethylphenyl)-pyrimidin-2-yl ester → N-tert-Butyl-3-{6-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoro-methanesulfonic acid 4-methyl-6-(4-trifluoromethylphenyl)-pyrimidin-2-yl ester | HCID 57468692 | — |
| Reactant | HCID 60209340 | HCID 60209340 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | N-tert-Butyl-3-{6-[4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-pyridin-2-yl}-benzenesulfonamide | HCID 57469110 | — |
Reaction Steps
A stirred mixture of trifluoro-methanesulfonic acid 4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl ester (Example A.62) (0.418 g, 1.08 mmol), N-tert-butyl-3-(6-tributylstannanyl-pyridin-2-yl)-benzenesulfonamide (Example F.6) (0.570 g, 0.98 mmol), tetrakis(triphenyl-phosphine)palladium (0.057 g, 5 mol %) in toluene (5 mL) was heated under reflux conditions for 18 h. Cooled to rt, extracted with ethyl acetate and water, dried the organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound after trituration with diethyl ether as a white solid (260 mg, 50%). MS (ISP) 527.3 [(M+H)+]; mp>250° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08183262B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-51743dc454414328b1d81a00e0157238 |
| Source note | uspto-grants-2012_05 |