Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Boc-1-(5-bromo-2-pyridyl)piperazine | HCID 11244775 | — |
| Reactant | 6-Bromo-3-chloropyrazin-2-amine | HCID 56965723 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 117732307 | HCID 117732307 | 29% |
Reaction Steps
Into a 2 L 4-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of compound 90e (42.8 g, 206 mmol) in 1,4-dioxane (1 L), compound 90b (80.0 g, 206 mmol), Pd(dppf)Cl2 (7.53 g, 10.3 mmol) and Cs2CO3 (167 g, 514 mmol). The reaction mixture was stirred overnight at 90° C. Upon cooling, the reaction was quenched with water (100 mL). The resulting mixture was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The resultant residue was purified by flash column chromatography on silica gel (DCM/MeOH (100:3 v/v)) to obtain compound 90f as a yellow solid (23.0 g, 29% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C18H23ClN6O2: 391.2 (M+H). found 391.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09249163B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-136fcc35055b407f892d7e9a44fa65c5 |
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| Source note | uspto-grants-2016_02 |
|---|
