Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Fluoro-4-methylsulfonylphenol | HCID 16128842 | — |
| Reactant | Tert-butyl 4-(4-chloro-1H-pyrazolo[3,4-D]pyrimidin-1-YL)piperidine-1-carboxylate | HCID 57964905 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 44514402 | HCID 44514402 | 47.5% |
Reaction Steps
A mixture of 2-fluoro-4-methanesulfonyl-phenol (Intermediate 1; 112 mg, 0.6 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 0.6 mmol) and potassium carbonate (180 mg, 1.3 mmol) in DMF (2 mL) was heated in a microwave oven at 160° C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture to give a precipitate which was filtered off and dissolved in ethyl acetate. The organic solution was dried (sodium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 20% ethyl acetate/hexanes, to give 4-[4-(2-fluoro-4-methane-sulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (140 mg, 47%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08188098B2 |
|---|
| Source dataset | uspto-grants-2012_05 |
|---|
| ORD ID | ord-0435519c8e634f0b81a7caf5d7a7d6e6 |
|---|
| Source note | uspto-grants-2012_05 |
|---|