Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 2734648 | — |
| Reactant | HCID 59457578 | HCID 59457578 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 16071665 | HCID 16071665 | 93.4% |
Reaction Steps
A mixture of 5-bromo-6-pyridin-3-ylpyrazin-2-amine (Preparation 6, 0.4 g, 1.59 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.424 g, 2.07 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloride dichloromethane complex (1:1) (76 mg, 0.095 mmol) and cesium carbonate (1.55 g, 4.77 mmol) in dioxane (14 mL) and water (3.72 mL) was heated to 150° C. for 10 minutes in the microwave oven. The mixture was partitioned between ethyl acetate and water. The organic layer was dried (MgSO4) and evaporated. Silica gel flash chromatography (95:5 dichloromethane/methanol) gave the title compound (0.37 g, 74%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07790728B2 |
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| Source dataset | uspto-grants-2010_09 |
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| ORD ID | ord-961bd91d8f8d4e248bea72075dfc8e37 |
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| Source note | uspto-grants-2010_09 |
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