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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

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantCesium carbonateHCID 10796—
Reactantmethyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoateHCID 70872676—
SolventAcetonitrileHCID 6342—
ProductMethyl 5-bromo-2-methyl-3-[methyl(oxan-4-yl)amino]benzoateHCID 7087250880%

Reaction Conditions

Temperature80 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08765732B2
Source datasetuspto-grants-2014_07
ORD IDord-16502569d525419389850d7c7ed30305
Source noteuspto-grants-2014_07