HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 5-Chloro-3-((5-(6-(piperazin-1-yl)pyridin-3-yl)furan-2-yl)methylene)indolin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(Piperazin-1-yl)pyridine-5-boronic acid, pinacol ester | HCID 16217946 | — |
| Reactant | 3-((5-Bromofuran-2-yl)methylene)-5-chloroindolin-2-one | HCID 66772829 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | 5-Chloro-3-((5-(6-(piperazin-1-yl)pyridin-3-yl)furan-2-yl)methylene)indolin-2-one | HCID 66772501 | — |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
To 3-((5-bromofuran-2-yl)methylene)-5-chloroindolin-2-one (50 mg, 0.155 mmol) in dioxane/water (5% water) was added Cs2CO3 (152 mg, 0.466 mmol) and 1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine (54 mg, 0.186 mmol). The mixture was degassed with nitrogen for 5 minutes then heated in microwave for 20 minutes at 120° C. The solution was diluted with water and the solid formed was isolated by filtration. The solid purified by HPLC to yield 5-chloro-3-((5-(6-(piperazin-1-yl)pyridin-3-yl)furan-2-yl)methylene)indolin-2-one. LCMS (M+1=407).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08124649B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-06293bae6b814f75bc97a76b5541d6e3 |
| Source note | uspto-grants-2012_02 |