Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 2734652 | — |
| Reactant | HCID 57497698 | HCID 57497698 | — |
| Catalyst | HCID 178418851 | HCID 178418851 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | HCID 86713611 | HCID 86713611 | 90.4% |
Reaction Steps
To a mixture of 1-(3-(7-chloroimidazo[1,2-a]pyridin-3-yl)phenyl)-3-(2,2,2-trifluoroethyl)urea (20 mg, 0.052 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (15 mg, 0.066 mmol) and cesium carbonate (51 mg, 0.156 mmol) in THF/H2O mixture (2/1, 0.75 ml) was added Pd(PtBu3)2 (3 mg, 0.005 mmol). The vial was degassed for 5 minutes then capped and heated to 125° C. for 20 minutes in a microwave. After cooling to ambient temperature, the reaction mixture was filtered through a celite pad and purified via flash chromatography (0-10% MeOH/DCM gradient containing 10% NH4OH) to yield the title compound (20 mg, 90% yield). MS (ES+) C22H18F3N5O requires: 425. found: 426 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09340514B2 |
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| Source dataset | uspto-grants-2016_05 |
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| ORD ID | ord-20d04a031aa340ebbb9e3cab57110cf2 |
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| Source note | uspto-grants-2016_05 |
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