Dimethylformamide → 2-Bromo-6-(3-fluorobenzyloxy)pyridine

Temperature

95 °C

To 2-bromo-6-fluoropyridine (176 mg, 1.000 mmol) was added DMF (1.5 ml) and (3-fluorophenyl)methanol (139 mg, 1.100 mmol) and cesium carbonate (391 mg, 1.200 mmol), and the resulting mixture reaction mixture was stirred at 95° C. for 6 hr, as the progress of the reaction mixture was followed by LCMS. The reaction mixture was cooled to room temperature, diluted with 120 ml of ethyl acetate, washed with saturated sodium bicarbonate (1×), water (1×), saturated salt solution (1×), dried over sodium sulfate, filtered and concentrated to yield a crude product which was purified by silica gel chromatography using a 12 g column eluting from 0%-20% ethyl acetate with hexane. The desired fractions were combined and concentrated to constant mass, giving 156 mg of the title compound as a free base. LCMS (m/z): 282.0/284.0 (MH+), retention time=1.19 min.

1. customthe resulting mixture reaction mixture
2. temperatureThe reaction mixture was cooled to room temperature
3. washwashed with saturated sodium bicarbonate (1×), water (1×), saturated salt solution (1×)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto yield a crude product which
8. customwas purified by silica gel chromatography
9. washeluting from 0%-20% ethyl acetate with hexane
10. concentrationconcentrated to constant mass

ORD record

ord-748363dcd8af4d3bb615c8673a49153b

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778951B2