Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methylboronic Acid | HCID 139377 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | HCID 71253861 | HCID 71253861 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Product | HCID 71254231 | HCID 71254231 | 39% |
Reaction Steps
A microwave reaction vial was charged with (R)-tert-butyl 1-(3-bromo-6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ylcarbamate (124.5 mg, 0.1867 mmol), Methyl boronic acid (111.76 mg, 1.867 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (15.2 mg, 0.01876 mmol), 1.00 M of Potassium acetate in Water (0.28 mL, 0.28 mmol), 1.00 M of Sodium carbonate in Water (0.28 mL, 0.28 mmol), and Acetonitrile (10 mL). The reaction mixture was heated under microwave at 150° C. for 5 minutes. The mixture was concentrated, and the residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford (R)-tert-butyl 1-(3-methyl-6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ylcarbamate (43.8 mg, 39%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09260425B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-3fbf273ceb004e4dbbe00bf1df652852 |
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| Source note | uspto-grants-2016_02 |
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