HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2035930Generated: October 31, 2026
Picolinic acid → 3-(4-(3-(1,1-Difluoroethyl)phenoxy)phenyl)-5-methylpyridin-2-amine
https://huagongshe.com/reaction/2035930
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Picolinic acid | HCID 1018 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1-Bromo-3-(1,1-difluoroethyl)benzene | HCID 22240121 | — |
| Reactant | 4-(2-Aminopyridin-3-yl)phenol | HCID 66748477 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 3-(4-(3-(1,1-Difluoroethyl)phenoxy)phenyl)-5-methylpyridin-2-amine | HCID 66748715 | 235% |
Reaction Steps
Copper(I) iodide (39.2 mg) was added to a mixture of picolinic acid (25.4 mg), 4-(2-aminopyridin-3-yl)phenol (206 mg), tripotassium phosphate (656 mg), 1-bromo-3-(1,1-difluoroethyl)benzene (239 mg) and DMSO (3 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 (165 mg) as a yellow amorphous 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-f68e569e5598495099b53d33b4da4d7f |
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| Source note | uspto-grants-2013_11 |
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