Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Ethyl-4-fluorobenzonitrile | HCID 57718439 | — |
| Reactant | HCID 178440406 | HCID 178440406 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 86700752 | HCID 86700752 | 54% |
Reaction Steps
Cesium carbonate (850 mg) was added to a solution of compound (5a) (200 mg) in DMSO (2.2 mL), and the mixture was heated to 130° C. The mixture was stirred for 10 minutes and 3-ethyl-4-fluorobenzonitrile (292 mg) was added thereto. The resulting mixture was stirred at the same temperature for 1.5 hours. After completion of the reaction, the reaction solution was allowed to standing still for cooling, and water was poured thereto. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and dried by the addition of anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was purified by neutral silica gel column chromatography (chloroform/ethyl acetate/methanol) to obtain compound (6a) (151.8 mg, yield 54%) as a white foamy substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09120780B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-519737d67aa24ea8b32b3c702b717ecf |
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| Source note | uspto-grants-2015_09 |
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