HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2035815Generated: November 1, 2026
Picolinic acid → 5-Chloro-3-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)-1,2-dihydropyridin-2-amine
https://huagongshe.com/reaction/2035815
Participants
| Role | Name | HCID | Charge |
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| Reactant | Picolinic acid | HCID 1018 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-Bromo-2-(trifluoromethyl)pyridine | HCID 23436950 | — |
| Reactant | 4-(2-Amino-5-chloropyridin-3-yl)phenol | HCID 66748004 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 5-Chloro-3-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)-1,2-dihydropyridin-2-amine | HCID 68280938 | 55.2% |
Reaction Steps
A mixture of 4-bromo-2-(trifluoromethyl)pyridine (282 mg), tripotassium phosphate (481 mg), picolinic acid (27.9 mg), copper(I) iodide (21.58 mg) and 4-(2-amino-5-chloropyridin-3-yl)phenol (250 mg) in DMSO (5 mL) was stirred at 140° C. under N2 overnight. The mixture was poured into sat. NH4Cl aq. and extracted with EtOAc. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (230 mg) as a pale yellow 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-eca71a48fc2b44f0b59f7f134c636165 |
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| Source note | uspto-grants-2013_11 |
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