Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Dichloromethane | HCID 6344 | — |
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 17750207 | — |
| Edukt | HCID 178432912 | HCID 178432912 | — |
| Lösungsmittel | Acetonitrile | HCID 6342 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | HCID 178487940 | HCID 178487940 | 37,1% |
Reaktionsschritte
To a suspension of 1-bromo-8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine (0.714 mmol, 280 mg) and 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.714 mmol, 178 mg) in dioxane (5 mL) was added aqueous 2M potassium carbonate (3.57 mmol, 1.78 mL). The mixture was degassed and put under a nitrogen atmosphere. Then 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (0.050 mmol, 40.4 mg) was added and the reaction mixture was heated to 89° C. After three hours the reaction mixture was diluted with acetonitrile (9 ml) and filtered over decalite. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel; gradient of dichloromethane to dichloromethane/methanol 5/1) to give 2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)aniline (115 mg).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08658794B2 |
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| Quelldatensatz | uspto-grants-2014_02 |
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| ORD ID | ord-13660ae0602c4d3fa3e8d6f6075710bc |
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| Quellennotiz | uspto-grants-2014_02 |
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