Methyl iodide → 7-Bromo-5-methylfuro[3,2-c]pyridin-4(5H)-one

Temperature

0 °C

To a suspension of 7-bromo-5H-furo[3,2-c]pyridin-4-one (250 mg, 1.17 mmol) in DMF (5 mL) cooled to 0° C. was added HNa (56 mg, 1.4 mmol, 60% dispersion in mineral oil) in three portions. After stirring at room temperature for 45 min, MeI (87 μL, 1.4 mmol) was added drop wise over five minutes. The reaction was allowed to warm up to rt stirred for 2 h. It was then cooled to 0° C. followed by addition of sat. aq. NH4Cl (5 mL) drop wise. The resulting mixture was extracted with EtOAc (3×5 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the title compound. LCMS: 227.9 (M+H)+

1. additionwas added HNa (56 mg, 1.4 mmol, 60% dispersion in mineral oil) in three portions
2. temperatureto warm up to rt
3. stirringstirred for 2 h
4. temperatureIt was then cooled to 0° C.
5. extractionThe resulting mixture was extracted with EtOAc (3×5 mL)
6. dry with materialThe combined organic layers were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography

ORD record

ord-efe70005b3a34eff81861174a1500416

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115114B2