HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1616366Generated: October 29, 2026
Methyl iodide → Methyl 5-bromo-2-methyl-3-[methyl(oxan-4-yl)amino]benzoate
https://huagongshe.com/reaction/1616366
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate | HCID 70872676 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Methyl 5-bromo-2-methyl-3-[methyl(oxan-4-yl)amino]benzoate | HCID 70872508 | 80% |
Reaction Steps
To a stirred solution of methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate (1.0 g, 3.15 mmol) in acetonitrile (15 mL), cesium carbonate (1.97 g, 6.10 mmol) and methyl iodide (2.15 g, 15.27 mmol) were added; resulting solution was heated at 80° C. for 20 h. The solution was cooled to room temperature, filtered, and the residue was washed with ethyl acetate. The filtrate was concentrated and the product purified by column chromatography to afford methyl 5-bromo-2-methyl-3-(methyl(tetrahydro-2H-pyran-4-yl)amino)benzoate (0.82 g, 80%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765732B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-16502569d525419389850d7c7ed30305 |
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| Source note | uspto-grants-2014_07 |
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