Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Amino-4-Methoxypyridine | HCID 10898715 | — |
| Reactant | 2,6-Dibromo-4-methylpyridine | HCID 11288174 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | HCID 178454861 | HCID 178454861 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86680797 | HCID 86680797 | 50% |
Reaction Steps
To a solution of 4-methoxypyridin-2-amine (620 mg, 5 mmol) and 2,6-dibromo-4-methylpyridine (1123 mg, 5.25 mmol) in dioxane (18 mL) was added 1,1′-bis(di-tertbutylphosphino)ferrocene palladium dichloride (280 mg, 0.5 mmol) and sodium tert-butoxide (437 mg, 5.25 mmol). Then the mixture stirred under microwave irradiation for 1.5 hours at 80° C. Then the mixture was poured into water (50 mL), and extracted with EtOAc (100 mL). The organic layer was washed with water (50 mL) and brine (50 mL), dried and concentrated. The residue purified by silica gel chromatography using a solvent system of 75% petroleum ether/EtOAc. The product containing fractions were collected and concentrated to give 6-bromo-N-(4-methoxypyridin-2-yl)-4-methylpyridin-2-amine (627 mg, 50%). MS ESI calcd for C12H12BrN3O [M+H]+ 294, found 294.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796310B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-5dec5d1a01694c98af1423ab20711dbd |
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| Source note | uspto-grants-2014_08 |
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