Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Isopropylphenol | HCID 7465 | — |
| Reactant | 2-Methylpyridine | HCID 7975 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-Amino-3-bromopyridine | HCID 817700 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 68280916 | HCID 68280916 | 11.4% |
Reaction Steps
A mixture of 3-bromopyridin-2-amine (1200 mg), tripotassium phosphate (2945 mg), 4-isopropylphenol (1134 mg), copper iodide(I) (132 mg) and picoline acid (171 mg) in DMSO (40 mL) was stirred under a nitrogen atmosphere at 80° C. overnight. The reaction mixture was added to saturated aqueous ammonium chloride solution, filtered through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (180.4 mg) as a pale-brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575154B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-f013a79d791a49b498bcd254271eca1d |
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| Source note | uspto-grants-2013_11 |
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