Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Picolinic acid | HCID 1018 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-Bromo-1-fluoro-2-methoxybenzene | HCID 13604909 | — |
| Reactant | HCID 50953296 | HCID 50953296 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 66748403 | HCID 66748403 | 44.6% |
Reaction Steps
Copper(I) iodide (95 mg) was added to a mixture of picolinic acid (61.5 mg), 4-(2-amino-5-methylpyridin-3-yl)phenol (500 mg), tripotassium phosphate (1590 mg), 4-bromo-1-fluoro-2-methoxybenzene (614 mg) and DMSO (8 mL). The mixture was stirred at 130° C. under nitrogen for 10 hr. The insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc). Silica-gel was added to the filtrate and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane) to give the title compound (361 mg) as pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08778934B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-fed440e0958f427dae091c7f21418768 |
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| Source note | uspto-grants-2014_07 |
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