HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonyl chloride → N-{3-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-phenyl}-methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | 3-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-phenylamine | HCID 24760587 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | N-{3-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-phenyl}-methanesulfonamide | HCID 68692477 | 19% |
Reaction Steps
To a stirred and cooled solution of 3-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-phenylamine (example 327) (0.400 g, 0.986 mmol) in EtOAc (4 mL) and sat. NaHCO3-sol. (2 mL) was added methanesulfonyl chloride (1.08 mL, 14.7 mmol) and the mixture was stirred at 23° C. for 2 h. Diluted with EtOAc, washed with sat. NaHCO3-sol. 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 EtOAc, followed by trituration with diethyl ether to give the title compound as a white solid (0.090 g, 19%). MS (ISP) 484.4 [(M+H)+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08183262B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-cb66876c44a943c7a8698874053194bd |
| Source note | uspto-grants-2012_05 |