HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2035790Generated: October 26, 2026
2-Methylpyridine → 3-[(7-Methoxynaphthalen-2-yl)oxy]pyridin-2-amine
https://huagongshe.com/reaction/2035790
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Methylpyridine | HCID 7975 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-Amino-3-bromopyridine | HCID 817700 | — |
| Reactant | 7-Methoxy-2-naphthol | HCID 853173 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | 3-[(7-Methoxynaphthalen-2-yl)oxy]pyridin-2-amine | HCID 66748540 | 36.1% |
Reaction Steps
A mixture of picoline acid (0.427 g), tripotassium phosphate (11.04 g), copper (I) iodide (0.660 g), 7-methoxynaphthalen-2-ol (6.04 g), 3-bromopyridin-2-amine (3 g) and DMSO (50 mL) was stirred under a nitrogen atmosphere at 140° C. overnight. Water was added, and the mixture was 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) and basic silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.667 g) 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-6daec4675cfa4e59b84d255a1033ab74 |
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| Source note | uspto-grants-2013_11 |
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