Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Quinoline-3-boronic acid | HCID 2734663 | — |
| Reactant | HCID 66733407 | HCID 66733407 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66738318 | HCID 66738318 | 59% |
Reaction Steps
To a 40 mL scintillation vial was charged 3-quinoline boronic acid (0.73 mmol, 127 mg), K3PO4 (1.46 mmol, 310 mg) and PdCl2(dppf).CH2Cl2 (0.049 mmol, 40 mg). To this mixture was added a solution of ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (335 mg, 0.49 mmol) in dioxane (9 mL). To this suspension was added distilled H2O (1 mL). The resulting solution was stirred at 100° C. for 18 hours. The reaction was concentrated in vacuo and then purified via silica gel chromatography (0% to 60% ethyl acetate in hexanes gradient) to yield ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (198 mg, 287 μmol, 59% yield) as yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08591943B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-093d2aa620f54a7dbb13e62ac5d239fc |
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| Source note | uspto-grants-2013_11 |
|---|
