HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 419520Generated: November 1, 2026
Sodium Carbonate → 4-[2-Methyl-5-(methyloxy)-4-nitrophenyl]pyridine
https://huagongshe.com/reaction/419520
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Reactant | HCID 59441753 | HCID 59441753 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-[2-Methyl-5-(methyloxy)-4-nitrophenyl]pyridine | HCID 59452649 | 57% |
Reaction Steps
A solution of 5-bromo-4-methyl-2-nitrophenyl methyl ether (6.0 g, 24.38 mmol), PdCl2(dppf)*DCM (1.43 g, 1.95 mmol) and 4-pyridylboronic acid (20.4 g, 165.8 mmol) in dioxane was deoxygenated by bubbling with N2 (g) for ca 15 min. To this solution was added degassed 2.0 N Na2CO3 (aq) (170 mL, 14.0 equiv.) and the resulting slurry was warmed to 80° C. for 24 h. The dioxane was removed under reduced pressure and the solids were dissolved in EtOAc and washed with H2O, dried (Na2SO4), and purified by flash chromatography to give the title compound of step A (2.81 g, 11.5 mmol, 57%). 1H NMR (400 MHz, CDCl3) δ ppm 8.72 (d, J=4.77 Hz, 2H), 7.79 (s, 1H), 7.22-7.31 (m, 2H), 6.90 (s, 1H), 3.95 (s, 3H), 2.22 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08093239B2 |
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| Source dataset | uspto-grants-2012_01 |
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| ORD ID | ord-463722b9566b486ea014b0a3e8f74ce3 |
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| Source note | uspto-grants-2012_01 |
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