Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 2734620 | — |
| Reactant | 3-Iodo-4-methoxypyridin-2-amine | HCID 24229206 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 86700075 | HCID 86700075 | 81.3% |
Reaction Steps
3-Iodo-4-methoxypyridin-2-amine (350 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (322 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane adduct (81 mg) and cesium fluoride (580 mg) were suspended in methanol (5.0 ml), and the suspension was heated under reflux at 80° C. for 19 hours. After leaving to cool, a saturated aqueous ammonium chloride solution was added, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [ethyl acetate:dichloromethane:methanol=5:5:1 (v/v)] to give 245 mg of the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08933103B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-8c244f861e66497b9fc123d87b1078ba |
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| Source note | uspto-grants-2015_01 |
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