Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 89174215 | HCID 89174215 | — |
| Reactant | HCID 117643958 | HCID 117643958 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 117643277 | HCID 117643277 | — |
Reaction Steps
3-Amino-3-methylpyridine (9 mg), cesium carbonate (45 mg), Pd2(dba)3 (10 mg), and Xantphos (12 mg) were added to a dioxane (3 ml) solution containing benzyl 4-((6-chloro-5-cyano-3-fluoropyridin-2-yl)amino)-3-(1,3-dioxoisoindolin-2-yl)piperidin-1-carboxylate (37 mg), followed by microwave irradiation (Initiator™, 160° C., 10 minutes, 2.45 GHz, 0-240 W). The obtained residue was filtered through Celite and filter cake was washed with ethyl acetate. Subsequently, the solvent was distilled away from the filtrate under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1). Yellow oily matter of benzyl 4-((5-cyano-3-fluoro-6-((5-methylpyridin-3-yl)amino)pyridin-2-yl)amino)-3-(1,3-dioxoisoindolin-2-yl)piperidin-1-carboxylate (28 mg) was thus obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051310B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-4492ee030fb946bfaf76680e36f1553c |
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| Source note | uspto-grants-2015_06 |
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