Methyl iodide → 3-Fluoro-6-(methylamino)pyridine

Temperature

40 °C

To a suspension of sodium hydride (60% dispersion in mineral oil, 117.8 mg, 4.91 mmol) in tetrahydrofuran (25 ml) was added a solution of 5-fluoropyridin-2-amine (500 mg, 4.46 mmol) in tetrahydrofuran (25 ml) at room temperature and the reaction mixture was stirred at 40° C. for 30 min. Then to the reaction mixture was added methyl iodide (696.9 mg, 4.91 mmol) at −40° C. and the resulting mixture was stand at room temperature overnight with stirring. The reaction was quenched by the addition of water and whole mixture was extracted with ethyl acetate. The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (4/1) to afford 129 mg (23%) of the title compound:

1. customat room temperature
2. customovernight
3. stirringwith stirring
4. customThe reaction was quenched by the addition of water and whole mixture
5. extractionwas extracted with ethyl acetate
6. dry with materialThe organic extracts were dried over sodium sulfate
7. concentrationconcentrated
8. customThe residue was purified
9. customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (4/1)

ORD record

ord-c5468c8452c34bfb9fe6d27e8ba84979

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084476B2