Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Fluoro-4-(methylsulfanyl)aniline | HCID 22025617 | — |
| Reactant | HCID 69005522 | HCID 69005522 | — |
| Reactant | (+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl | HCID 86595863 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69009937 | HCID 69009937 | — |
Reaction Steps
2-Fluoro-4-methylsulfanyl-phenylamine (1.01 equivalents), palladium(II) acetate (0.10 equivalents), rac-2,2-bis(diphenylphosphino)-1,1′-binaphthyl (0.15 equivalents), and cesium carbonate (1.50 equivalents) are added to a solution of 6-chloro-7-methylpyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester (1.00 equivalent) in toluene in a sealed vial. After stirring 10 minutes, the mixture is heated to 80° C. After 24 hours, the reaction mixture is cooled to room temperature and diluted with EtOAc. The resulting precipitate is filtered and washed with EtOAc. The filtrate is diluted with EtOAc and washed with water. The aqueous layer is re-extracted with EtOAc. The combined organic layers are washed with brine, dried (MgSO4) and concentrated. The product is purified by flash chromatography as necessary.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07576072B2 |
|---|
| Source dataset | uspto-grants-2009_08 |
|---|
| ORD ID | ord-4249cf1c88a745d69eb36390fbdb178a |
|---|
| Source note | uspto-grants-2009_08 |
|---|