Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 45786526 | — |
| Reactant | HCID 67494530 | HCID 67494530 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 67494482 | HCID 67494482 | 61% |
Reaction Steps
To a pressure tube were charged benzyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate (1 g, 2.85 mmol), 2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.2 g, 4.1 mmol), Pd(PPh3)4 (164 mg, 0.14 mmol), DME (20 mL) and 2 M Na2CO3 (10 mL). The mixture was briefly degassed with Argon and the tube was capped and heated at 80° C. for 15 hours. On cooling, H2O (40 mL) and EtOAc (100 mL) and aqueous layer was extracted with EtOAc (3×) and combined organic layers were washed with brine once and dried (MgSO4). After concentration in vacuo the residue was purified on silica gel. Elution with EtOAc/Hexanes (0-30%) gave the title compound (1.33 g, 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08591943B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-2804fc286ba84b3290b6d4cb61b93073 |
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| Source note | uspto-grants-2013_11 |
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