Methyl iodide → 2,3-Dichloro-5-(methoxymethyl)pyridine

To a solution of (5,6-dichloro-pyridin-3-yl)-methanol (356 mg, 2.0 mmol, Aldrich) and iodomethane (0.25 mL, 4.0 mmol, Aldrich) in DMF (3.0 mL) was added NaH (120 mg, 3.0 mmol, Aldrich, 60% dispersion in mineral oil) portionwise with stirring at room temperature. The mixture was stirred for 30 min at room temperature, saturated aqueous solution of NH4Cl (10 mL) was added, and the mixture was extracted with EtOAc (2×30 mL). The combined organic phases were washed with water (5 mL) and brine (5 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with 20% EtOAc/hexane to give the title compound. MS (ESI, pos. ion) m/z: 192 (M+1).

1. stirringThe mixture was stirred for 30 min at room temperature
2. extractionthe mixture was extracted with EtOAc (2×30 mL)
3. washThe combined organic phases were washed with water (5 mL) and brine (5 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customThe solvent was removed in vacuo
7. customthe residue was purified by silica gel column chromatography
8. washeluting with 20% EtOAc/hexane

ORD record

ord-ab8f679c87744f4898f6c0e8f04b3a42

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582761B2