Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5-Methylpyridine-3-boronic acid | HCID 2762708 | — |
| Reactant | HCID 178462119 | HCID 178462119 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178430475 | HCID 178430475 | 43.1% |
Reaction Steps
Trans-4-(4-Bromo-benzenesulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Example 115, 100 mg, 0.206 mmol), Pd(dppf)Cl2.DCM (34 mg, 0.04 mmol), 2M Na2CO3 (1 ml, 2.06 mmol) and 5-methyl-3-pyridine boronic acid (51 mg, 0.37 mmol) were dissolved in DMF (1-2 ml) under N2. The reaction mixture was microwaved at 160° C. for 20 min., after which LCMS indicated that the reaction was complete. The mixture was diluted with EtOAc and washed with H2O (×2). The organic layer was concentrated in vacuo, and the crude material purified via column chromatography using a biotage SP1 25+S column with a gradient of 80-100% EtOAc in heptane. Product fractions combined and concentrated to give the title compound as a white solid (44 mg, 43%). MS MH+ 496.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08394858B2 |
|---|
| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-189312bd3d904128a597e6bf2716f0b8 |
|---|
| Source note | uspto-grants-2013_03 |
|---|
