Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| Reactant | 4-(Trifluoromethoxy)phenylboronic acid | HCID 2734386 | — |
| Reactant | HCID 178480720 | HCID 178480720 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178480724 | HCID 178480724 | 72% |
Reaction Steps
An amount of 6-bromo-4-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-4H-isoquinoline-1,3-dione (0.1 g, 0.2267 mmol) in 1 mL of N,N′-dimethylformamide is added to 4-(trifluoromethoxy)phenylboronic acid (0.07 g, 0.34 mmol), 0.032 g (0.034 mmol) of tris(dibenzylideneacetone)dipalladium(0), tri(t-butyl)phosphine (0.014 g, 0.068 mmol) and cesium carbonate (0.148 g, 0.4534 mmol). The reaction mixture is stirred at 130 oC under N2 for 15 min. Mass spectroscopy suggested the completion of the reaction. The mixture is diluted with chloroform and filtered through Celite. The filtrate is evaporated to dryness and purified by column chromatography using 5% methanol/methylene chloride as eluent to yield 85 mg (72% yield) of the title compound as orange solid. MS (ESI) m/z 523.2 (M+H)+1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07713994B2 |
|---|
| Source dataset | uspto-grants-2010_05 |
|---|
| ORD ID | ord-d7ffa9c1d5bf40d8ac670d0dfc06df7e |
|---|
| Source note | uspto-grants-2010_05 |
|---|