Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | HCID 86716497 | HCID 86716497 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86716511 | HCID 86716511 | — |
Reaction Steps
A mixture of tert-butyl (1-{4-[3-phenyl-6,8-dibromoimidazo[1,2-b]pyridazin-2-yl]phenyl}cyclobutyl)carbamate that was prepared in a manner analgous to that described for Intermediate Example Int-6 (0.25 g, 0.42 mmol), (4-fluorophenyl)boronic acid (0.12 g, 0.84 mmol, 2.0 equiv.), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride (0.034 g, 0.042 mmol, 0.1 equiv.) and sodium carbonate (0.13 g, 1.25 mmol, 3.0 equiv) in a mixture of water (0.6 mL) and dioxane (4.5 mL) was irradiated in a microwave apparatus at 110° C. for 60 min. The resulting reaction mixture was added to water (25 mL). The aqueous mixture was extracted with DCM (3×25 mL). The combined organic phases were washed with an aqueous NaOH solution (2 N), dried (Na2SO4 anh.) and concentrated under reduced pressure to give impure tert-butyl (1-{4-[6,8-bis(4-fluorophenyl)-3-phenylimidazo[1,2-b]pyridazin-2-yl]phenyl}cyclobutyl)carbamate (0.39 g) which was used without further purification:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206185B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-8b42fb57b3f64765b4fb1450b747591c |
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| Source note | uspto-grants-2015_12 |
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