HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 73426445, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2,2,2-Trifluoroethyl trifluoromethanesulfonate | HCID 80366 | — |
| Reactant | HCID 73426362 | HCID 73426362 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 73426445 | HCID 73426445 | — |
Reaction Steps
To a solution of N-(3,3-dimethyl-2-oxoindolin-6-yl)-3-fluoroisonicotinamide (example 72, 78 mg, 261 μmol) in DMF (700 μl) under an argon atmosphere was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (66.5 mg, 39.6 μl, 287 μmol) and cesium carbonate (93.4 mg, 287 μmol). After 3 hours at room temperature the reaction mixture was poured into water and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (with 10% ammonia) as eluent followed by trituration with diethyl ether/heptane. The title compound was obtained as white foam (36 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09221816B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-219a830c901d4d4bb49b8f99e928757b |
| Source note | uspto-grants-2015_12 |