Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 2794719 | — |
| Reactant | HCID 69929724 | HCID 69929724 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86667836 | HCID 86667836 | — |
Reaction Steps
To a 10-20 mL microwave vessel was charged ethyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)methyl)cyclohexanecarboxylate (Int-4j, 2.94 g, 4.27 mmol), 6-chloropyridine-3-boronic acid pinacol ester (1.07 g, 4.48 mmol), K3PO4 (2.72 g, 12.81 mmol), and PdCl2(dppf)2.CH2Cl2 (349 mg, 0.43 mmol). To this was added 9:1 1,4-dioxane:H2O. The vial was flushed with argon, sealed, and stirred at 100° C. overnight. After 18 hours, the reaction was cooled to room temperature and diluted with DCM. The reaction was washed with water and the aqueous phase was extracted again with DCM. The combined organics were dried over Na2SO4 and the residue purified via silica gel chromatography to yield title compound as yellowish oil that crystallizes over time. Yield=1.93 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08609675B2 |
|---|
| Source dataset | uspto-grants-2013_12 |
|---|
| ORD ID | ord-3fa2f78c4b0f40da9f100d382a9de832 |
|---|
| Source note | uspto-grants-2013_12 |
|---|
