Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N,N-Dimethylethylenediamine | HCID 66053 | — |
| Reactant | HCID 67501505 | HCID 67501505 | — |
| Reactant | HCID 178440405 | HCID 178440405 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86700750 | HCID 86700750 | 47% |
Reaction Steps
A solution of compound (1a) (200 mg), copper(I) iodide (50 mg), cesium carbonate (430 mg), 4-bromo-2-(tert-butylamino)benzonitrile (250 mg), and N,N-dimethylethane-1,2-diamine (0.11 mL) in 1,4-dioxane (3.3 mL) was stirred overnight under heating at 150° C. After completion of the reaction, the reaction solution was allowed to standing still for cooling, filtered, and the filtrate 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 (1b) (146 mg, yield 47%) 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-80c288ed4dca471e9a163f8461efda98 |
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| Source note | uspto-grants-2015_09 |
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