Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 2-Fluorophenylboronic acid | HCID 2734354 | — |
| Reactant | Potassium phosphate, tribasic, monohydrate | HCID 22031701 | — |
| Reactant | HCID 86664786 | HCID 86664786 | — |
| 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 67494490 | HCID 67494490 | 95% |
Reaction Steps
To tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-chloropyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate (2.25 g, 3.3 mmol) in Dioxane (24 ml) and H2O (6 ml) was added the 2-fluorophenylboronic acid (0.92 g, 6.6 mmol), PdCl2(dppf)2.CH2Cl2 (0.32 g, 0.39 mmol) and K3PO4.H2O (1.7 g, 8.2 mmol). The reaction was heated at 100° C. for 16 hours, at which time LC/MS analysis confirmed full consumption of starting material. On cooling, H2O (100 ml) and EtOAc (100 ml) were added and organics were extracted with EtOAc (4×50 ml), dried (Na2SO4) and concentrated in vacuo to give a crude product. Gradient column chromatography on silica eluting with 0% to 100% EtOAc/hexanes gave tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-(2-fluorophenyl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate (2.3 g, 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08591943B2 |
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| Source dataset | uspto-grants-2013_11 |
|---|
| ORD ID | ord-2833b0be210b4ba2b4e13c0020c72149 |
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| Source note | uspto-grants-2013_11 |
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