Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Methylpiperazine | HCID 53167 | — |
| Reactant | 1,3-dibromo-5-nitrobenzene | HCID 238711 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67248827 | HCID 67248827 | 45% |
Reaction Steps
In a oven-dried flask and under a nitrogen atmosphere, were placed 3,5-dibromonitrobenzene (500 mg, 1.78 mmol), (+/−) BINAP (110 mg, 0.1 eq), Cs2CO3 (1.62 g, 3 eq), Pd2dba3 (81 mg, 0.11 eq) and 10 mL of dry 1,4-dioxane. N-Methylpiperazine (0.47 mL, 2.4 eq) was added and the mixture was stirred at 90° C. for 48 h. The solution was filtered through a celite pad and evaporated. The residue was purified by flash chromatography on silica gel (DCM/MeOH/NH4OH//95/5/1) to yield expected compound as an orange solid (258 mg, 45% yield). m/z (MALDI-TOF) 320.2 [M+H]+;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680095B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-51d94bd0df9140beb02af5a5ef2f4d49 |
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| Source note | uspto-grants-2014_03 |
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