Methyl 1-methoxy-4-bromo-2-naphthoate → Methyl 4-[(6-chloropyridin-3-yl)methyl]-1-methoxy-2-naphthoate

Temperature

90 °C

To a solution of methyl 4-bromo-1-methoxy-2-naphthoate (see Example 2, 0.500 g, 1.69 mmol) in 5 mL of THF under an atmosphere of nitrogen was added (2-chloro-5-pyridyl)methylzinc chloride (0.5 M in THF, 10.2 mL, 5.08 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.050 g, 0.043 mmol). The reaction was heated at 90° C. for 2 hours, then cooled to room temperature and diluted with water and ethyl acetate. The mixture was filtered through celite and the organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes to provide methyl 4-[(6-chloropyridin-3-yl)methyl]-1-methoxy-2-naphthoate that gave a mass ion (ES+) of 342.0 for [M+H]+.

1. temperaturecooled to room temperature
2. filtrationThe mixture was filtered through celite
3. washthe organic solution was washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified via silica gel chromatography
8. washeluting with 0-20% ethyl acetate in hexanes

ORD record

ord-f5382ea356e744ffb8e72d7975cfbcba

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08883850B2